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878671-94-4

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878671-94-4 Usage

General Description

"1-Naphthalenamine, 4-cyclopropyl-" is a chemical compound that is synthesized from naphthalenamine usage in advanced organic chemistry. The term "1-Naphthalenamine" refers to the base structure of the compound, which consists of a naphthalene (a type of hydrocarbon) linked to an amine (-NH2) group. The "4-cyclopropyl-" indicates that a cyclopropyl group, a ring of three carbon atoms, is attached to the fourth carbon in the naphthalene ring. This chemical exhibits several applications in different research areas and industries due to its particular properties. However, there is limited data available on its biological effects and safety. Likely, protective measures and caution are advised during handling.

Check Digit Verification of cas no

The CAS Registry Mumber 878671-94-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,7,8,6,7 and 1 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 878671-94:
(8*8)+(7*7)+(6*8)+(5*6)+(4*7)+(3*1)+(2*9)+(1*4)=244
244 % 10 = 4
So 878671-94-4 is a valid CAS Registry Number.
InChI:InChI=1/C13H13N/c14-13-8-7-10(9-5-6-9)11-3-1-2-4-12(11)13/h1-4,7-9H,5-6,14H2

878671-94-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-cyclopropylnaphthalen-1-amine

1.2 Other means of identification

Product number -
Other names 4-Cyclopropyl-1-Naphthalenamine

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:878671-94-4 SDS

878671-94-4Synthetic route

1-cyclopropyl-4-nitronaphthalene
878671-93-3

1-cyclopropyl-4-nitronaphthalene

1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Conditions
ConditionsYield
Stage #1: 1-cyclopropyl-4-nitronaphthalene With iron hydroxide oxide In water at 80℃; for 0.5h;
Stage #2: With hydrazine In water for 2h; Solvent; Temperature; Reagent/catalyst; Time;
96%
With ammonium chloride; zinc In tetrahydrofuran; water for 10h; Reflux;89.1%
With ammonium chloride; zinc In tetrahydrofuran; water Reagent/catalyst; Reflux;87%
4-Bromo-1-naphthylamine
2298-07-9

4-Bromo-1-naphthylamine

cyclopropylboronic acid
411235-57-9

cyclopropylboronic acid

1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Conditions
ConditionsYield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 6h; Suzuki Coupling; Inert atmosphere;95.3%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 6h; Inert atmosphere;95.3%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 12h; Inert atmosphere;83.6%
1-bromo-4-cyclopropylnaphthalene
127971-24-8

1-bromo-4-cyclopropylnaphthalene

1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In N,N-dimethyl-formamide at 100℃; for 28h; Solvent; Reagent/catalyst; Temperature; Autoclave; Green chemistry;80%
1-cyclopropyl-naphthalene
25033-19-6

1-cyclopropyl-naphthalene

1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium nitrite / 2.5 h / 0 °C
2: hydrogen / palladium 10% on activated carbon / ethanol
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / 0 - 20 °C
2: palladium on activated charcoal; hydrogen
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / water; dichloromethane
2: palladium on activated charcoal; hydrogen; oxalic acid / ethanol
View Scheme
Multi-step reaction with 2 steps
1: nitric acid
2: iron perchlorate hexahydrate; hydrazine hydrate / ethanol / Reflux
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; nitric acid / 7 h / 20 °C / Cooling with ice
2: zinc; ammonium chloride / tetrahydrofuran; water / 10 h / Reflux
View Scheme
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 0 - 20 °C
2: sodium nitrite / 2.5 h / 0 °C
3: hydrogen / palladium 10% on activated carbon / ethanol
View Scheme
Multi-step reaction with 3 steps
1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 0 - 5 °C
2: nitric acid / 0 - 20 °C
3: palladium on activated charcoal; hydrogen
View Scheme
Multi-step reaction with 3 steps
1.1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / Cooling with ice
1.2: 44 h / 20 °C / Reflux; Inert atmosphere
2.1: acetic acid; nitric acid / 7 h / 20 °C / Cooling with ice
3.1: zinc; ammonium chloride / tetrahydrofuran; water / 10 h / Reflux
View Scheme
1-amino-naphthalene
134-32-7

1-amino-naphthalene

cyclopropylboronic acid
411235-57-9

cyclopropylboronic acid

1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); phosphoric acid In water; toluene at 100℃; for 12h; Inert atmosphere;
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

phenyl chloroformate
1885-14-9

phenyl chloroformate

C20H17NO2

C20H17NO2

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at -10℃; for 1h; Temperature; Inert atmosphere;98.5%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

1,1'-Thiocarbonyldiimidazole
6160-65-2

1,1'-Thiocarbonyldiimidazole

(1-cyclopropylnaphthalen-4-yl)isothiocyanate
878671-95-5

(1-cyclopropylnaphthalen-4-yl)isothiocyanate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h;96.2%
In dichloromethane at 20℃; for 1h;80%
In dichloromethane at 20℃;
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

2-nitro-3-(trifluoromethylsulfonyloxy)pyridine
146336-72-3

2-nitro-3-(trifluoromethylsulfonyloxy)pyridine

N-(4-cyclopropylnaphthalen-1-yl)-2-nitropyridin-3-amine

N-(4-cyclopropylnaphthalen-1-yl)-2-nitropyridin-3-amine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 90℃; for 36h; Inert atmosphere;95.3%
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In toluene at 90℃; for 36h; Inert atmosphere;33.3%
carbon disulfide
75-15-0

carbon disulfide

1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

(1-cyclopropylnaphthalen-4-yl)isothiocyanate
878671-95-5

(1-cyclopropylnaphthalen-4-yl)isothiocyanate

Conditions
ConditionsYield
Stage #1: carbon disulfide; 1-amino-4-cyclopropylnaphthalene With potassium carbonate In water; N,N-dimethyl-formamide at 15℃; for 3.5h;
Stage #2: With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water; N,N-dimethyl-formamide at 0℃; for 1h;
Stage #3: With water; sodium hydroxide In dichloromethane; N,N-dimethyl-formamide for 2h;
94%
Stage #1: 1-amino-4-cyclopropylnaphthalene With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃;
Stage #2: carbon disulfide In toluene at 20℃; for 7.5h;
Stage #3: With p-toluenesulfonyl chloride In toluene at 0℃; for 3h; Reflux;
86.3%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

thiophosgene
463-71-8

thiophosgene

(1-cyclopropylnaphthalen-4-yl)isothiocyanate
878671-95-5

(1-cyclopropylnaphthalen-4-yl)isothiocyanate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h;86%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h;86%
Stage #1: 1-amino-4-cyclopropylnaphthalene; thiophosgene With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h;
Stage #2: With hydrogenchloride In dichloromethane; water
86%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

C8H15N3O

C8H15N3O

3-(3-buten-1-yl)-4-(4-cyclopropylnaphth-1-yl)-4H-1,2,4-triazole

3-(3-buten-1-yl)-4-(4-cyclopropylnaphth-1-yl)-4H-1,2,4-triazole

Conditions
ConditionsYield
With acetic acid In acetonitrile at 120℃; Inert atmosphere;81%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

4-Pentenoic acid hydrazide
86538-23-0

4-Pentenoic acid hydrazide

3-(3-buten-1-yl)-4-(4-cyclopropylnaphth-1-yl)-4H-1,2,4-triazole

3-(3-buten-1-yl)-4-(4-cyclopropylnaphth-1-yl)-4H-1,2,4-triazole

Conditions
ConditionsYield
Stage #1: 4-Pentenoic acid hydrazide With N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 50℃; for 2h;
Stage #2: 1-amino-4-cyclopropylnaphthalene With acetic acid for 12h; Reflux;
78%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

diazodimedone
1807-68-7

diazodimedone

4-cyclopropyl-9,9-dimethyl-9,10-dihydro-7H-benzo[kl]acridin-11(8H)-one

4-cyclopropyl-9,9-dimethyl-9,10-dihydro-7H-benzo[kl]acridin-11(8H)-one

Conditions
ConditionsYield
With {Ir(η5-C5Me5)(CH3CN)3}{SbF6}2; acetic acid In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;78%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

diformylhydrazine
628-36-4

diformylhydrazine

4-(4-cyclopropylnaphthalene)-1,2,4-triazole

4-(4-cyclopropylnaphthalene)-1,2,4-triazole

Conditions
ConditionsYield
With pyridine; chloro-trimethyl-silane In toluene at 20℃; for 2h; Solvent; Reagent/catalyst; Temperature; Reflux;78%
With pyridine; chloro-trimethyl-silane at 20℃; for 2h; Reflux;70%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

C13H12ClN

C13H12ClN

Conditions
ConditionsYield
With N-chloro-succinimide; acetic acid at 20℃; for 16h;64.47%
With N-chloro-succinimide; acetic acid at 20℃; for 16h;64.47%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

3-chloro-2-nitropyridine
54231-32-2

3-chloro-2-nitropyridine

N-(4-cyclopropylnaphthalen-1-yl)-2-nitropyridin-3-amine

N-(4-cyclopropylnaphthalen-1-yl)-2-nitropyridin-3-amine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 90℃; for 12.25h; Inert atmosphere;60.6%
With palladium acetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere;60.6%
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol
878671-96-6

5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C
2.2: 60 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 12 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 20 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 50 h
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

2-((5-amino-4-(4-cyclopropyl-naphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid methyl ester

2-((5-amino-4-(4-cyclopropyl-naphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C
2.2: 60 h / 50 °C
3.1: potassium carbonate / 24.08 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide
3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating
4: N,N-dimethyl-formamide / 14 - 22 °C
View Scheme
Multi-step reaction with 5 steps
1: toluene; water
2: potassium hydroxide
3: N,N-dimethyl-formamide
4: sodium hydroxide / N,N-dimethyl-formamide; water / Heating
5: N,N-dimethyl-formamide / 14 - 22 °C
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane / 12 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 50 °C
3: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane / 20 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 50 h
3: potassium carbonate / N,N-dimethyl-formamide / 20 °C
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid

2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C
2.2: 60 h / 50 °C
3.1: potassium carbonate / 24.08 h / 20 °C
4.1: sodium nitrite; N-benzyl-N,N,N-triethylammonium chloride; Bromoform; dichloro-acetic acid / 3 h / 20 °C
5.1: water; lithium hydroxide / ethanol; tetrahydrofuran / 0.83 h / 0 °C
5.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 6 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide / 50 - 55 °C
3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C
4: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale
5: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale
6: sodium hydroxide; water / toluene / 18 - 25 °C
View Scheme
Multi-step reaction with 6 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide
3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating
4: N,N-dimethyl-formamide / 14 - 22 °C
5: copper(ll) bromide; potassium nitrite / acetonitrile / 14 - 20 °C
6: sodium hydroxide; water / toluene / 18 - 25 °C
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid methyl ester

2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C
2.2: 60 h / 50 °C
3.1: potassium carbonate / 24.08 h / 20 °C
4.1: sodium nitrite; N-benzyl-N,N,N-triethylammonium chloride; Bromoform; dichloro-acetic acid / 3 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide / 50 - 55 °C
3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C
4: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale
5: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale
View Scheme
Multi-step reaction with 5 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide
3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating
4: N,N-dimethyl-formamide / 14 - 22 °C
5: copper(ll) bromide; potassium nitrite / acetonitrile / 14 - 20 °C
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid sodium salt
1151516-14-1

2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid sodium salt

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C
2.2: 60 h / 50 °C
3.1: potassium carbonate / 24.08 h / 20 °C
4.1: sodium nitrite; N-benzyl-N,N,N-triethylammonium chloride; Bromoform; dichloro-acetic acid / 3 h / 20 °C
5.1: water; lithium hydroxide / ethanol; tetrahydrofuran / 0.83 h / 0 °C
5.2: 0 °C / pH 7
6.1: sodium hydroxide / ethanol; water / 0.25 h / 10 °C
View Scheme
Multi-step reaction with 6 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide / 50 - 55 °C
3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C
4: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale
5: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale
6: sodium hydroxide / toluene; water / 18 - 25 °C / Large scale
View Scheme
Multi-step reaction with 6 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide
3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating
4: N,N-dimethyl-formamide / 14 - 22 °C
5: copper(ll) bromide; potassium nitrite / acetonitrile / 14 - 20 °C
6: sodium hydroxide / toluene; water / 18 - 25 °C / Large scale
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Reaxys ID: 26486083

Reaxys ID: 26486083

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide / 50 - 55 °C
3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C
4: N,N-dimethyl-formamide
5: N-Bromosuccinimide / tetrahydrofuran
View Scheme
Multi-step reaction with 6 steps
1: toluene; water
2: potassium hydroxide
3: N,N-dimethyl-formamide / 50 - 55 °C
4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C
5: N,N-dimethyl-formamide
6: N-Bromosuccinimide / tetrahydrofuran
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

3-amino-4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione
878671-96-6

3-amino-4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide
3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating
View Scheme
Multi-step reaction with 4 steps
1: toluene; water
2: potassium hydroxide
3: N,N-dimethyl-formamide
4: sodium hydroxide / N,N-dimethyl-formamide; water / Heating
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

Reaxys ID: 26486087

Reaxys ID: 26486087

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide / 50 - 55 °C
3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C
4: N,N-dimethyl-formamide
View Scheme
Multi-step reaction with 5 steps
1: toluene; water
2: potassium hydroxide
3: N,N-dimethyl-formamide / 50 - 55 °C
4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C
5: N,N-dimethyl-formamide
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

(1-cyclopropylnaphthalen-4-yl)isothiocyanate
878671-95-5

(1-cyclopropylnaphthalen-4-yl)isothiocyanate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene; water
2: potassium hydroxide
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

C15H17N5S*ClH
1533519-90-2

C15H17N5S*ClH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide
View Scheme
Multi-step reaction with 3 steps
1: toluene; water
2: potassium hydroxide
3: N,N-dimethyl-formamide
View Scheme
1-amino-4-cyclopropylnaphthalene
878671-94-4

1-amino-4-cyclopropylnaphthalene

N-(4-cyclopropylnaphthalen-1-yl)-2-formylhydrazine-1-thiocarboxamide
1533519-86-6

N-(4-cyclopropylnaphthalen-1-yl)-2-formylhydrazine-1-thiocarboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C
2: N,N-dimethyl-formamide / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: toluene; water
2: potassium hydroxide
3: N,N-dimethyl-formamide / 50 - 55 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / water; N,N-dimethyl-formamide / 3.5 h / 15 °C
1.2: 1 h / 0 °C
1.3: 2 h
2.1: ethyl acetate / 2 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: ethyl acetate
2: ethanol
View Scheme

878671-94-4Relevant articles and documents

Arylazolyl(azinyl)thioacetanilides: Part 19: Discovery of Novel Substituted Imidazo[4,5-b]pyridin-2-ylthioacetanilides as Potent HIV NNRTIs Via a Structure-based Bioisosterism Approach

Li, Xiao,Huang, Boshi,Zhou, Zhongxia,Gao, Ping,Pannecouque, Christophe,Daelemans, Dirk,De Clercq, Erik,Zhan, Peng,Liu, Xinyong

, p. 241 - 253 (2016)

With the continuation of our unremitting efforts toward the discovery of potent HIV-1 NNRTIs, a series of novel imidazo[4,5-b]pyridin-2-ylthioacetanilides were designed, synthesized, and evaluated for their antiviral activities through combining bioisosteric replacement and structure-based drug design. Almost all of the title compounds displayed moderate to good activities against wild-type (wt) HIV-1 strain with EC50 values ranging from 0.059 to 1.41 μm in a cell-based antiviral assay. Thereinto, compounds 12 and 13 were the most active two analogues possessing an EC50 value of 0.059 and 0.073 μm against wt HIV-1, respectively, which was much more effective than the control drug nevirapine (EC50 = 0.26 μm) and comparable to delavirdine (EC50 = 0.038 μm). In addition, one selected compound showed a remarkable reverse transcriptase inhibitory activity compared to nevirapine and etravirine. In the end of this manuscript, preliminary structure–activity relationships (SARs) and molecular modeling studies were detailedly discussed, which may provide valuable insights for further optimization.

Thienopyrimidone acyl sulfonamide derivative as well as preparation method and application thereof

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Paragraph 0032-0036, (2021/09/04)

The invention relates to a thienopyrimidone acyl sulfonamide derivative as well as a preparation method and application thereof. The thienopyrimidone acyl sulfonamide derivative has a structure as shown in a formula I. The invention also relates to a preparation method of the compound with the structure as shown in the general formula I and a pharmaceutical composition. The invention also provides application of the compound in preparation of anti-gout drugs.

Novel Human Urate Transporter 1 Inhibitors as Hypouricemic Drug Candidates with Favorable Druggability

Zhao, Tong,Meng, Qing,Sun, Zhuosen,Chen, Yanyu,Ai, Wei,Zhao, Zean,Kang, Dongwei,Dong, Yue,Liang, Ruipeng,Wu, Ting,Pang, Jianxin,Liu, Xinyong,Zhan, Peng

, p. 10829 - 10854 (2020/11/09)

Lesinurad, a human urate transporter 1 (URAT1) inhibitor approved as a medication for the treatment of hyperuricemia associated with gout in 2015, can cause liver and renal toxicity. Here, we modified all three structural components of lesinurad by applying scaffold hopping, bioisosterism, and substituent-decorating strategies. In a mouse model of acute hyperuricemia, 21 of the synthesized compounds showed increased serum uric acid (SUA)-reducing activity; SUA was about 4-fold lower in animals treated with 44, 54, and 83 compared with lesinurad or benzbromarone. In the URAT1 inhibition assay, 44 was over 8-fold more potent than lesinurad (IC50: 1.57 μM vs 13.21 μM). Notably, 83 also displayed potent inhibitory activity (IC50 = 31.73 μM) against GLUT9. Furthermore, we also preliminarily explored the effect of chirality on the potency of the promising derivatives 44 and 54. Compounds 44, 54, and 83 showed favorable drug-like pharmacokinetics and appear to be promising candidates for the treatment of hyperuricemia and gout.

Lesinurad analogue and its preparation method and medical use

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Paragraph 0046; 0047; 0048; 0053; 0054, (2019/05/28)

The invention relates to a lesinurad analog as shown in the general formula (I), its preparation method, a pharmaceutical composition containing the derivative and an application of the pharmaceutical composition used as a therapeutic agent, especially as a medicine for treating hyperuricemia and gout, wherein definition of each substituent group in the general formula (I) is as the same as definition in the specification.

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