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4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]is a complex chemical compound that belongs to the group of organic compounds known as thiazolequinolines. Its molecular structure comprises a thiazole ring – an aromatic organic ring containing a sulfur atom and a nitrogen atom – fused with a methylated quinoline ring. Additionally, it has a methoxy group attached to the quinoline ring.

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  • 2-(4-Isopropylthiazol-2-Yl)-7-Methoxy-8-Methylquinolin-4-Ol

    Cas No: 923289-21-8

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  • 923289-21-8 Structure
  • Basic information

    1. Product Name: 4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-
    2. Synonyms: 4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-;2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol;7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-;7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-4-Quinolinol;7-Methoxy-8-Methyl-2-[4-isopropylthiazol-2-yl]-4-hydroxy-quinoline;7-methoxy-8-methyl-2-(4-propan-2-yl-1,3-thiazol-2-yl)-1h-quinolin-4-one;2-(2-isopropylthiazol-4-yl)-7-methoxy-8-methylquinolin-4-ol;2-(4-Isopropylthiazol-2-yl)
    3. CAS NO:923289-21-8
    4. Molecular Formula: C17H18N2O2S
    5. Molecular Weight: 314.4
    6. EINECS: 1308068-626-2
    7. Product Categories: Heterocycles
    8. Mol File: 923289-21-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 518 ºC at 760 mmHg
    3. Flash Point: 267.1 ºC
    4. Appearance: /
    5. Density: 1.240
    6. Vapor Pressure: 2.37E-11mmHg at 25°C
    7. Refractive Index: 1.635
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: 7.96±0.61(Predicted)
    11. CAS DataBase Reference: 4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-(923289-21-8)
    13. EPA Substance Registry System: 4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-(923289-21-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 923289-21-8(Hazardous Substances Data)

923289-21-8 Usage

Uses

Used in Biochemistry Research:
4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]is used as a research compound for exploring its potential applications and properties in the field of biochemistry.
Used in Organic Chemistry Research:
4-Quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]is used as a research compound for investigating its chemical behavior and interactions in the field of organic chemistry.

Check Digit Verification of cas no

The CAS Registry Mumber 923289-21-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,2,3,2,8 and 9 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 923289-21:
(8*9)+(7*2)+(6*3)+(5*2)+(4*8)+(3*9)+(2*2)+(1*1)=178
178 % 10 = 8
So 923289-21-8 is a valid CAS Registry Number.
InChI:InChI=1/C17H18N2O2S/c1-9(2)13-8-22-17(19-13)12-7-14(20)11-5-6-15(21-4)10(3)16(11)18-12/h5-9H,1-4H3,(H,18,20)

923289-21-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 7-methoxy-8-methyl-2-(4-propan-2-yl-1,3-thiazol-2-yl)-1H-quinolin-4-one

1.2 Other means of identification

Product number -
Other names 2-(4-Isopropyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:923289-21-8 SDS

923289-21-8Synthetic route

N-(6-acetyl-2-methyl-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide
923289-20-7

N-(6-acetyl-2-methyl-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Stage #1: N-(6-acetyl-2-methyl-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide With potassium tert-butylate In tert-butyl alcohol for 18h; Reflux; Inert atmosphere;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃;
99%
With potassium tert-butylate In tert-butyl alcohol for 18h; Inert atmosphere; Reflux;99%
With potassium tert-butylate In tert-butyl alcohol at 100℃; for 8h;90%
2-(4,7-dimethoxy-8-methylquinoline-2-yl)-4-isopropylthiazole

2-(4,7-dimethoxy-8-methylquinoline-2-yl)-4-isopropylthiazole

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
With hydrogenchloride In water for 14h; Inert atmosphere; Reflux;80%
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: bromine / methanol / 3 h / -30 - 20 °C / Inert atmosphere
2.1: ethanol / 1.5 h / Inert atmosphere; Reflux
3.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
4.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux
View Scheme
1-(2-amino-4-methoxy-3-methyl-phenyl)ethanone
912347-94-5

1-(2-amino-4-methoxy-3-methyl-phenyl)ethanone

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux
View Scheme
4-isopropylthiazole-2-carboxylic acid
1108658-73-6

4-isopropylthiazole-2-carboxylic acid

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: oxalyl dichloride / dichloromethane / 4.5 h / 0 - 20 °C
2: acetone / 4.5 h / 0 - 20 °C
3: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C
View Scheme
C9H14BrNO2S

C9H14BrNO2S

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
2.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux
View Scheme
1-bromo-3-methyl-2-butanone
19967-55-6

1-bromo-3-methyl-2-butanone

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethanol / 1.5 h / Inert atmosphere; Reflux
2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
3.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 5 steps
1: ethanol / 2 h / 75 °C
2: lithium hydroxide monohydrate / methanol / 3.5 h / 0 - 20 °C
3: oxalyl dichloride / dichloromethane / 4.5 h / 0 - 20 °C
4: acetone / 4.5 h / 0 - 20 °C
5: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C
View Scheme
2-methyl-3-methoxyaniline
19500-02-8

2-methyl-3-methoxyaniline

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: boron trichloride / dichloromethane; para-xylene / 0.5 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 0 °C / Inert atmosphere
1.3: 19.75 h / 0 - 70 °C / Inert atmosphere
2.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 7 steps
1: methanol / 4 h / 20 °C
2: Eaton′s Reagent / 1 h / 50 °C
3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
4: ammonia / methanol / 20 °C
5: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
6: methanol / 48 h / 20 °C
7: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 7 steps
1: methanol / 4 h / 20 °C
2: Eaton′s Reagent / 1 h / 50 °C
3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
4: magnesium chloride / acetonitrile / 20 h / 80 °C
5: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere
6: manganese(IV) oxide / 24 h / Reflux
7: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 8 steps
1: methanol / 4 h / 20 °C
2: Eaton′s Reagent / 1 h / 50 °C
3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
4: ammonia / methanol / 20 °C
5: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
6: potassium carbonate / methanol / 24 h / 50 °C
7: isopropyl alcohol / 24 h / 100 °C
8: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
N-(S)-(1-hydroxy-3-methylbutan-2-yl)-4,7-dimethoxy-8-methylquinoline-2-carboxamide

N-(S)-(1-hydroxy-3-methylbutan-2-yl)-4,7-dimethoxy-8-methylquinoline-2-carboxamide

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere
2: manganese(IV) oxide / 24 h / Reflux
3: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
2-(4,7-dimethoxy-8-methylquinoline-2-yl)-4-isopropyl-4,5-dihydrothiazole

2-(4,7-dimethoxy-8-methylquinoline-2-yl)-4-isopropyl-4,5-dihydrothiazole

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: manganese(IV) oxide / 24 h / Reflux
2: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
4,7-dimethoxy-8-methylquinoline-2-carboxamide

4,7-dimethoxy-8-methylquinoline-2-carboxamide

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
2: methanol / 48 h / 20 °C
3: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 4 steps
1: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
2: potassium carbonate / methanol / 24 h / 50 °C
3: isopropyl alcohol / 24 h / 100 °C
4: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
4,7-dimethoxy-8-methylquinoline-2-carboxthioamide

4,7-dimethoxy-8-methylquinoline-2-carboxthioamide

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 48 h / 20 °C
2: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / methanol / 24 h / 50 °C
2: isopropyl alcohol / 24 h / 100 °C
3: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
dimethyl 2-(3-methoxy-2-methylphenylamino)-2-butenedioate
801281-88-9

dimethyl 2-(3-methoxy-2-methylphenylamino)-2-butenedioate

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Eaton′s Reagent / 1 h / 50 °C
2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
3: ammonia / methanol / 20 °C
4: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
5: methanol / 48 h / 20 °C
6: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 6 steps
1: Eaton′s Reagent / 1 h / 50 °C
2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
3: magnesium chloride / acetonitrile / 20 h / 80 °C
4: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere
5: manganese(IV) oxide / 24 h / Reflux
6: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 7 steps
1: Eaton′s Reagent / 1 h / 50 °C
2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
3: ammonia / methanol / 20 °C
4: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
5: potassium carbonate / methanol / 24 h / 50 °C
6: isopropyl alcohol / 24 h / 100 °C
7: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
4,5-dihydro-4-isopropyl-2-(4,7-dimethoxy-8-methylquinolin-2-yl)thiazol-4-ol

4,5-dihydro-4-isopropyl-2-(4,7-dimethoxy-8-methylquinolin-2-yl)thiazol-4-ol

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: isopropyl alcohol / 24 h / 100 °C
2: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
methyl 4-hydroxy-7-methoxy-8-methylquinoline-2-carboxylate
801281-89-0

methyl 4-hydroxy-7-methoxy-8-methylquinoline-2-carboxylate

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
2: ammonia / methanol / 20 °C
3: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
4: methanol / 48 h / 20 °C
5: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
2: magnesium chloride / acetonitrile / 20 h / 80 °C
3: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere
4: manganese(IV) oxide / 24 h / Reflux
5: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 6 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
2: ammonia / methanol / 20 °C
3: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
4: potassium carbonate / methanol / 24 h / 50 °C
5: isopropyl alcohol / 24 h / 100 °C
6: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
methyl 4,7-dimethoxy-8-methylquinoline-2-carboxylate

methyl 4,7-dimethoxy-8-methylquinoline-2-carboxylate

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ammonia / methanol / 20 °C
2: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
3: methanol / 48 h / 20 °C
4: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 4 steps
1: magnesium chloride / acetonitrile / 20 h / 80 °C
2: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere
3: manganese(IV) oxide / 24 h / Reflux
4: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 5 steps
1: ammonia / methanol / 20 °C
2: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere
3: potassium carbonate / methanol / 24 h / 50 °C
4: isopropyl alcohol / 24 h / 100 °C
5: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux
View Scheme
4-(1-methylethyl)thiazole-2-carboxylic acid ethyl ester
156589-82-1

4-(1-methylethyl)thiazole-2-carboxylic acid ethyl ester

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium hydroxide monohydrate / methanol / 3.5 h / 0 - 20 °C
2: oxalyl dichloride / dichloromethane / 4.5 h / 0 - 20 °C
3: acetone / 4.5 h / 0 - 20 °C
4: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C
View Scheme
4-isopropylthiazole-2-carbonyl chloride
923289-59-2

4-isopropylthiazole-2-carbonyl chloride

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 4.5 h / 0 - 20 °C
2: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C
View Scheme
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

4-chloro-2-isopropylthiazolyl-7-methoxy-8-methylquinoline

4-chloro-2-isopropylthiazolyl-7-methoxy-8-methylquinoline

Conditions
ConditionsYield
With NaOH In trichlorophosphate96%
With sodium hydroxide; trichlorophosphate4.11 g (91%)
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester
74844-91-0, 114676-69-6, 135042-17-0, 227935-38-8, 102195-79-9

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

C28H35N3O6S
923604-80-2

C28H35N3O6S

Conditions
ConditionsYield
With 2-(diphenylphosphino)pyridine; di-isopropyl azodicarboxylate In tetrahydrofuran at -15 - 20℃; for 17h;85%
With 2-(diphenylphosphino)pyridine; di-tert-butyl-diazodicarboxylate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;80%
With di-isopropyl azodicarboxylate In tetrahydrofuran at -15 - 20℃; Mitsunobu reaction;
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C32H44N4O11S

C32H44N4O11S

C43H57N5O8S

C43H57N5O8S

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 50℃;80%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C32H44N4O10S

C32H44N4O10S

C43H57N5O8S

C43H57N5O8S

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 50℃;80%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

(1R,2R,4S)-1-benzyl 2-methyl 4-hydroxycyclopentane-1,2-dicarboxylate
1042695-89-5

(1R,2R,4S)-1-benzyl 2-methyl 4-hydroxycyclopentane-1,2-dicarboxylate

C32H34N2O6S
1042695-85-1

C32H34N2O6S

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; for 2h; Product distribution / selectivity; Mitsunobu reaction;75%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Product distribution / selectivity; Mitsunobu reaction;71%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C26H35BrN2O8S2
1551161-65-9

C26H35BrN2O8S2

C37H48N4O7S2
1551161-70-6

C37H48N4O7S2

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 75℃;74%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

methyl-2-fluoro-1-((1R,2R,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxamido)-cis-2-vinylcyclopropanecarboxylate

methyl-2-fluoro-1-((1R,2R,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxamido)-cis-2-vinylcyclopropanecarboxylate

methyl 2-fluoro-1-((1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-cis-2-vinylcyclopropanecarboxylate

methyl 2-fluoro-1-((1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-cis-2-vinylcyclopropanecarboxylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4h; Mitsunobu Displacement; Inert atmosphere;72%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

methyl (1R,2R,4R)-2-[5-hexen-1-yl-(methyl)carbamoyl]-4-hydroxycyclopentanecarboxylate
1042695-84-0

methyl (1R,2R,4R)-2-[5-hexen-1-yl-(methyl)carbamoyl]-4-hydroxycyclopentanecarboxylate

methyl (1R,2R,4S)-2-[5-hexen-1-yl(methyl)carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate
1042695-87-3

methyl (1R,2R,4S)-2-[5-hexen-1-yl(methyl)carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; for 19 - 20h; Product distribution / selectivity;71%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

ethyl(2S,6S,13aS,14aR,16aS)-6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
744250-80-4

ethyl(2S,6S,13aS,14aR,16aS)-6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

(2R,6S,13aS,14aR,16aS)-6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)carboxylic acid

(2R,6S,13aS,14aR,16aS)-6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)carboxylic acid

Conditions
ConditionsYield
Stage #1: 8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol; ethyl(2S,6S,13aS,14aR,16aS)-6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #2: With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 18h;
Stage #3: With hydrogenchloride In tetrahydrofuran; methanol
61%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C21H32N2O8S
1218999-00-8

C21H32N2O8S

C37H46N4O7S
1218999-01-9

C37H46N4O7S

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 70℃;58%
(1R,2S)-1-{[(1R,2R,4S)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester
922727-93-3

(1R,2S)-1-{[(1R,2R,4S)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate
923604-56-2

ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4.5h;56%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4.5h;56%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15 - 20℃; Mitsunobu reaction;
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C22H34N2O5

C22H34N2O5

C39H50N4O6S

C39H50N4O6S

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4.5h;56%
C25H32BrN3O9S2
874124-85-3

C25H32BrN3O9S2

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C36H45N5O8S2
1285533-29-0

C36H45N5O8S2

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 75℃;45%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C19H28N2O8S
1218998-86-7

C19H28N2O8S

C35H42N4O7S
1218998-87-8

C35H42N4O7S

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;30%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

(1R,4R,6S,15R,18R)-18-(4-bromobenzenesulfonyloxy)-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.4.0.0]nonadec-7-ene-4-carboxylic acid methyl ester

(1R,4R,6S,15R,18R)-18-(4-bromobenzenesulfonyloxy)-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.4.0.0]nonadec-7-ene-4-carboxylic acid methyl ester

(1R,4R,6S,15R,18S)-18-[2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.4.0.0]nonadec-7-ene-4-carboxylic acid methyl ester

(1R,4R,6S,15R,18S)-18-[2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.4.0.0]nonadec-7-ene-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: 8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol; (1R,4R,6S,15R,18R)-18-(4-bromobenzenesulfonyloxy)-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.4.0.0]nonadec-7-ene-4-carboxylic acid methyl ester at 70℃; for 40h;
Stage #2: With potassium carbonate In 1-methyl-pyrrolidin-2-one at 85℃; for 4h;
27%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C18H29N3O5

C18H29N3O5

(1R,4S,14S,Z)-ethyl 4-(2-(2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)ethyl)-7-methyl-3,6-dioxo-2,5,7-triazabicyclo[12.1.0]pentadec-12-ene-1-carboxylate
1108660-17-8

(1R,4S,14S,Z)-ethyl 4-(2-(2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)ethyl)-7-methyl-3,6-dioxo-2,5,7-triazabicyclo[12.1.0]pentadec-12-ene-1-carboxylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;26%
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

18-hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxyric acid ethyl ester
923274-86-6

18-hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxyric acid ethyl ester

C44H53N5O7S

C44H53N5O7S

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Product distribution / selectivity;
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C21H32N2O5
1079097-27-0

C21H32N2O5

C38H48N4O6S
1079097-45-2

C38H48N4O6S

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine at -20 - 20℃; Mitsunobu reaction;
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C22H34N2O5
923289-03-6

C22H34N2O5

C39H50N4O6S
1079097-40-7

C39H50N4O6S

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine at -20 - 20℃; Mitsunobu reaction;
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C25H31BrN2O8S

C25H31BrN2O8S

C37H46N4O7S
1218998-94-7

C37H46N4O7S

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 15h; Sealed tube;
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-6-[(1-pyrrolidinylcarbonyl)amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-6-[(1-pyrrolidinylcarbonyl)amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere
2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere
3.2: 18 h / 40 °C / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.2: Inert atmosphere
View Scheme
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

C45H59N7O8S2

C45H59N7O8S2

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere
2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere
3.2: 18 h / 40 °C / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.2: Inert atmosphere
View Scheme
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-6-[(1-piperidinylcarbonyl)amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-6-[(1-piperidinylcarbonyl)amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere
2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere
3.2: 18 h / 40 °C / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.2: Inert atmosphere
View Scheme
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-6-{[(4-hydroxy-1-piperidinyl)carbonyl]amino}-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16 ,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-6-{[(4-hydroxy-1-piperidinyl)carbonyl]amino}-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16 ,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere
2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere
3.2: 18 h / 40 °C / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.2: Inert atmosphere
View Scheme
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
923289-21-8

8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-6-({[4-(hydroxymethyl)-1-piperidinyl]carbonyl}amino)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-6-({[4-(hydroxymethyl)-1-piperidinyl]carbonyl}amino)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere
2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere
3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere
3.2: 18 h / 40 °C / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.2: Inert atmosphere
View Scheme

923289-21-8Relevant articles and documents

Macrocyclic serine protease inhibitors, pharmaceutical compositions thereof, and their use for treating HCV infections

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Page/Page column 101; 102; 104, (2016/06/28)

Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, and pharmaceutical compositions and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

COMPOUNDS AS HEPATITIS C INHIBITORS AND USES THEREOF IN MEDICINE

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, (2016/09/22)

Provided herein are compounds as hepatitis C inhibitors and uses thereof in medicine. Specifically, provided herein is a compound of Formula (I) or a stereoisomer, a tautomer, an enantiomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or hepatitis C diseases. Also provided herein are a pharmaceutically acceptable composition containing such compound and a method of treating HCV infection or hepatitis C diseases comprising administering the compound or pharmaceutical composition thereof disclosed herein.

Synthesis of 2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol; A quinoline building block for simeprevir synthesis

Rádl, Stanislav,Rezková, Hana,Obadalová, Iva,Srbek, Jan,B?ichá?, Ji?í,Pekárek, Tomá?

, p. 899 - 908 (2014/04/03)

Two synthetic approaches to the achiral quinoline fragment of simeprevir are described. Both approaches are based on the synthesis of methyl 4-hydroxy-7-methoxy-8-methylquinoline-2-carboxylate, protection of its 4-hydroxyl group, and construction of the thiazole ring from the ester group at the 2-position. The last step is acid deprotection of the 4-hydroxyl protecting group. Georg Thieme Verlag Stuttgart. New York.

Discovery of novel urea-based hepatitis C protease inhibitors with high potency against protease-inhibitor-resistant mutants

Kazmierski, Wieslaw M.,Hamatake, Robert,Duan, Maosheng,Wright, Lois L.,Smith, Gary K.,Jarvest, Richard L.,Ji, Jing-Jing,Cooper, Joel P.,Tallant, Matthew D.,Crosby, Renae M.,Creech, Katrina,Wang, Amy,Li, Xianfeng,Zhang, Suoming,Zhang, Yong-Kang,Liu, Yang,Ding, Charles Z.,Zhou, Yasheen,Plattner, Jacob J.,Baker, Stephen J.,Bu, Wei,Liu, Liang

, p. 3021 - 3026 (2012/06/01)

The macrocyclic urea 2, a byproduct in the synthesis of benzoxaborole 1, was identified to be a novel and potent HCV protease inhibitor. We further explored this motif by synthesizing additional urea-based inhibitors and by characterizing them in replicase HCV protease-resistant mutants assay. Several compounds, exemplified by 12, were found to be more potent in HCV replicon assays than leading second generation inhibitors such as danoprevir and TMC-435350. Additionally, following oral administration, inhibitor 12 was found in rat liver in significantly higher concentrations than those reported for both danoprevir and TMC-435350, suggesting that inhibitor 12 has the combination of anti-HCV and pharmacokinetic properties that warrants further development of this series.

MACROCYCLIC SERINE PROTEASE INHIBITORS USEFUL AGAINST VIRAL INFECTIONS, PARTICULARLY HCV

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Page/Page column 147, (2011/02/24)

Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula (Ia) or (Ib), pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

MACROCYCLIC SERINE PROTEASE INHIBITORS

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Page/Page column 121, (2009/03/07)

Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

NOVEL MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS REPLICATION

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, (2009/10/31)

The embodiments provide compounds of the general Formulae I, II, III, IV, V, VI, VII, and X, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

HCV INHIBITING MACROCYCLIC PHOSPHONATES AND AMIDOPHOSPHATES

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Page/Page column 83, (2008/12/08)

Inhibitors of HCV replication of Formula (I) the /V-oxides, salts, and stcreochcmically isomeric forms thereof; pharmaceutical compositions containing compounds (1) and processes for preparin compounds (I). The side chain R2 is an amidophosphate or a phosphonate group and X, R1, R3, E and n are as defined in the application.

POLYMORPHIC FORMS OF A MACROCYCLIC INHIBITOR OF HCV

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Page/Page column 29-30, (2008/12/07)

Provided are crystalline forms of the compound of formula (I), which is a macrocyclic inhibitor of HCV, processes for the preparation thereof, and pharmaceutical compositions comprising these crystalline forms.

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