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284462-37-9

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284462-37-9 Usage

Chemical Properties

Light-Brown Solid

Uses

Sorafenib intermediate

Check Digit Verification of cas no

The CAS Registry Mumber 284462-37-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,4,4,6 and 2 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 284462-37:
(8*2)+(7*8)+(6*4)+(5*4)+(4*6)+(3*2)+(2*3)+(1*7)=159
159 % 10 = 9
So 284462-37-9 is a valid CAS Registry Number.
InChI:InChI=1/C13H13N3O2/c1-15-13(17)12-8-11(6-7-16-12)18-10-4-2-9(14)3-5-10/h2-8H,14H2,1H3,(H,15,17)

284462-37-9SDS

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 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1.2 Other means of identification

Product number -
Other names 4-[(4-aminomethyl)phenoxy]-2-pyridine carbonic acid methylamide

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:284462-37-9 SDS

284462-37-9Synthetic route

4-amino-phenol
123-30-8

4-amino-phenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 25℃; for 1h;97%
Stage #1: 4-amino-phenol With potassium hydroxide for 0.166667h;
Stage #2: 4-chloro-N-methylpicolinamide for 1.5h;
97.3%
With 18-crown-6 ether In acetonitrile for 1.5h; Reagent/catalyst; Solvent; Temperature; Reflux;92.5%
4-(4-nitro)benzyloxy-2-carbonylmethylaminopyridine
864272-34-4

4-(4-nitro)benzyloxy-2-carbonylmethylaminopyridine

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
With hydrogen; nickel In tetrahydrofuran; methanol at 20℃; Product distribution / selectivity;97%
With palladium 10% on activated carbon; hydrogen In methanol at 35℃; under 2068.65 Torr; for 2h;95%
With palladium 10% on activated carbon; hydrogen In methanol at 40 - 50℃; under 7500.75 Torr; Solvent; Autoclave;92.5%
Stage #1: 4-(4-nitro)benzyloxy-2-carbonylmethylaminopyridine With iron(III) chloride hexahydrate; pyrographite In ethanol at 90℃; for 0.5h; Sonication;
Stage #2: With hydrazine hydrate In ethanol Sonication;
70%
With ammonia; tetra(n-butyl)ammonium hydrogensulfate; iron20.1 g
4-nitro-phenol
100-02-7

4-nitro-phenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Stage #1: 4-nitro-phenol; 4-chloro-N-methylpicolinamide With potassium carbonate for 4h; Reflux;
Stage #2: With iron(III) chloride; hydrazine hydrate; FeCl3/C In ethanol for 3h; Concentration; Reflux;
94.6%
Stage #1: 4-nitro-phenol With potassium hydroxide for 0.166667h; Heating; Green chemistry;
Stage #2: 4-chloro-N-methylpicolinamide for 1.5h; Green chemistry;
Stage #3: With iron(III) chloride; pyrographite; hydrazine hydrate In ethanol; 1,2-dichloro-ethane for 3h; Reflux; Green chemistry;
94.5%
C12H9ClN2O2

C12H9ClN2O2

methylamine
74-89-5

methylamine

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide at -5 - 10℃; for 1.5h; Large scale;84.1%
4-chloropyridine-2-carbohydrazide
73771-11-6

4-chloropyridine-2-carbohydrazide

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Stage #1: With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
Stage #2: 4-chloropyridine-2-carbohydrazide With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;
80%
4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: 4-chloro-N-methylpicolinamide With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;
71%
With potassium tert-butylate; potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 10h; Product distribution / selectivity;
Multi-step reaction with 2 steps
1: ethyl acetate
2: ammonia; iron; tetra(n-butyl)ammonium hydrogensulfate
View Scheme
4-chloro-N,N-dimethylpyridine-2-carboxamide
114780-06-2

4-chloro-N,N-dimethylpyridine-2-carboxamide

4-amino-phenol
123-30-8

4-amino-phenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

A

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B

4-(4-aminophenoxy)-N,N-dimethylpicolinamide
284462-86-8

4-(4-aminophenoxy)-N,N-dimethylpicolinamide

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 4-chloro-N,N-dimethylpyridine-2-carboxamide; 4-chloro-N-methylpicolinamide With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;
A 70%
B 69%
4-(3-aminophenoxy)-N-methylpicolinamide
284462-78-8

4-(3-aminophenoxy)-N-methylpicolinamide

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2-amino-3-methoxynaphthalene
67291-63-8

2-amino-3-methoxynaphthalene

A

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B

5-tert-Butyl-2-(2,5-dimethylpyrrolyl)-aniline

5-tert-Butyl-2-(2,5-dimethylpyrrolyl)-aniline

3-(4-aminophenoxy)-N-methylbenzamide
284462-56-2

3-(4-aminophenoxy)-N-methylbenzamide

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

of4-aminophenol

of4-aminophenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

A

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B

of4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline

of4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline

Conditions
ConditionsYield
With potassium tert-butylate; potassium carbonate In N,N-dimethyl-formamide
2-Picolinic acid
98-98-6

2-Picolinic acid

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 17.5 h / 50 °C / Inert atmosphere; Reflux
2.1: tetrahydrofuran; methanol / 0 - 20 °C
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C
3.2: 6 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride; N,N-dimethyl-formamide / 16 h / 72 °C
2: 5 h / 3 °C
3: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide
View Scheme
Multi-step reaction with 3 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 50 °C / Inert atmosphere; Reflux
2.1: tetrahydrofuran; methanol / 2 h / 0 - 20 °C
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C
3.2: 6 h / 80 °C / Inert atmosphere
View Scheme
4-chloro-pyridine-2-carbonyl chloride
53750-66-6

4-chloro-pyridine-2-carbonyl chloride

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; methanol / 0 - 20 °C
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C
2.2: 6 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; methanol / 2 h / 0 - 20 °C
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C
2.2: 6 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: 2 h / 30 °C
2.1: tetrahydrofuran; methanol / 3 h / 2 - 20 °C
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
3.2: 10 h / 80 - 85 °C
View Scheme
4-chloro-2-pyridine carboxylic acid chloride hydrochloride

4-chloro-2-pyridine carboxylic acid chloride hydrochloride

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 5 h / 3 °C
2: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide
View Scheme
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; methanol / 4 h / 0 - 3 °C
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 20 °C
2.2: 8 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1.1: tetrahydrofuran / 16.42 h / 0 - 20 °C / Inert atmosphere
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2.02 h / Inert atmosphere
2.2: 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; methanol / 4 h / 0 - 3 °C
2.1: potassium tert-butylate / DMF (N,N-dimethyl-formamide) / 2 h / 20 °C
2.2: 8 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: water; tetrahydrofuran
2: sodium hydride / dimethyl sulfoxide / 3 h / 100 °C
View Scheme
4-Chloro-pyridine-2-carboxylic acid methyl ester
24484-93-3

4-Chloro-pyridine-2-carboxylic acid methyl ester

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; methanol / 3 h / 2 - 20 °C
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
2.2: 10 h / 80 - 85 °C
View Scheme
Multi-step reaction with 2 steps
1: water / 3 h / 20 °C
2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: water; tetrahydrofuran / 3 h / 20 °C
2: potassium tert-butylate / N,N-dimethyl-formamide / 3 h / 100 °C
View Scheme
4-chloropicolinamide
99586-65-9

4-chloropicolinamide

4-amino-phenol
123-30-8

4-amino-phenol

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
Stage #2: 4-chloropicolinamide With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;
4‐(4‐aminophenoxy)‐2‐pyridine carboxylic acid
1012058-77-3

4‐(4‐aminophenoxy)‐2‐pyridine carboxylic acid

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / chloroform / 1.5 h / Reflux; Large scale
2: potassium carbonate / water; N,N-dimethyl-formamide / 1.5 h / -5 - 10 °C / Large scale
View Scheme
4-bromo-2-cyanopyridine
62150-45-2

4-bromo-2-cyanopyridine

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / tetrahydrofuran; water / 5.5 h / Reflux; Large scale
2: thionyl chloride / chloroform / 1.5 h / Reflux; Large scale
3: potassium carbonate / water; N,N-dimethyl-formamide / 1.5 h / -5 - 10 °C / Large scale
View Scheme
4-amino-phenol
123-30-8

4-amino-phenol

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / tetrahydrofuran; water / 5.5 h / Reflux; Large scale
2: thionyl chloride / chloroform / 1.5 h / Reflux; Large scale
3: potassium carbonate / water; N,N-dimethyl-formamide / 1.5 h / -5 - 10 °C / Large scale
View Scheme
sorafenib
284461-73-0

sorafenib

A

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

B

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With hydrogenchloride; water; sodium chloride at 0℃; for 3h; pH=1.5; pH-value;
4-chloropicolinic acid
5470-22-4

4-chloropicolinic acid

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 15.5 h / 0 - 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 16.42 h / 0 - 20 °C / Inert atmosphere
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2.02 h / Inert atmosphere
3.2: 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / ethanol; water / 4 h / 120 °C
2: ethyl acetate
3: ammonia; iron; tetra(n-butyl)ammonium hydrogensulfate
View Scheme
N-methylpyridine-2-carboxamide
6144-78-1

N-methylpyridine-2-carboxamide

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: fluorine; sulfuric acid / 25 °C
2: caesium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C
3: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 35 °C / 2068.65 Torr
View Scheme
ethyl 4-chloropyridine-2-carboxylate
64064-56-8

ethyl 4-chloropyridine-2-carboxylate

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: chlorobenzene / 4 h / 130 °C / UV-irradiation
2.1: ethanol; sodium hydroxide / 1 h / 20 °C
3.1: thionyl chloride / 0.17 h / 85 °C / Sonication
4.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice
4.2: 0.5 h / Cooling with ice
5.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication
5.2: Sonication
View Scheme
ethyl 4-(4-nitrophenoxy)picolinate

ethyl 4-(4-nitrophenoxy)picolinate

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethanol; sodium hydroxide / 1 h / 20 °C
2.1: thionyl chloride / 0.17 h / 85 °C / Sonication
3.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice
3.2: 0.5 h / Cooling with ice
4.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication
4.2: Sonication
View Scheme
4-(4-nitrophenoxy)picolinic acid

4-(4-nitrophenoxy)picolinic acid

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / 0.17 h / 85 °C / Sonication
2.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice
2.2: 0.5 h / Cooling with ice
3.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication
3.2: Sonication
View Scheme
4-(4-nitrophenoxy)pyridine-2-carbonyl chloride

4-(4-nitrophenoxy)pyridine-2-carbonyl chloride

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane; water / 0.33 h / Cooling with ice
1.2: 0.5 h / Cooling with ice
2.1: iron(III) chloride hexahydrate; pyrographite / ethanol / 0.5 h / 90 °C / Sonication
2.2: Sonication
View Scheme
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

(4-chloro-3-trifluoromethyl aniline)carboxylic acid allyl ester

(4-chloro-3-trifluoromethyl aniline)carboxylic acid allyl ester

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With 1-Methylpyrrolidine In dichloromethane at 30℃; for 24h; Solvent; Temperature;97.6%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

2-fluoro-5-(trifluoromethyl)benzoic acid
115029-23-7

2-fluoro-5-(trifluoromethyl)benzoic acid

4-(4-(2-fluoro-5(trifluoromethyl)benzamido)phenoxy)-N-methylpicolinamide
1313019-74-7

4-(4-(2-fluoro-5(trifluoromethyl)benzamido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
Stage #1: 2-fluoro-5-(trifluoromethyl)benzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.516667h;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In N,N-dimethyl-formamide for 12h;
97%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1-fluoro-3-isocyanatobenzene
404-71-7

1-fluoro-3-isocyanatobenzene

4-(4-(3-(3-fluorophenyl)ureido)phenoxy)-N-methylpicolinamide

4-(4-(3-(3-fluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
In dichloromethane for 48h;97%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With zirconia grinding balls In acetonitrile for 4h; Milling;96%
In ethyl acetate at 20 - 30℃; Large scale;94.2%
In dichloromethane93%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

sorafenib tosylate

sorafenib tosylate

Conditions
ConditionsYield
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In ethyl acetate at 40 - 71℃; for 0.5h;
Stage #2: toluene-4-sulfonic acid In water; ethyl acetate at 71℃; for 0.666667h; Product distribution / selectivity;
96%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In butanone at 20 - 85℃;
Stage #2: toluene-4-sulfonic acid In butanone at 20℃;
88%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In tetrahydrofuran at 25 - 64℃; for 0.5h;
Stage #2: toluene-4-sulfonic acid In tetrahydrofuran at 64℃; Product distribution / selectivity;
81.6%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

para-fluorophenyl isocyanate
1195-45-5

para-fluorophenyl isocyanate

4-[4-[[[[4-fluorophenyl]amino]carbonyl]amino]phenoxy]-N-methylpyridine-2-carboxamide
1285533-80-3

4-[4-[[[[4-fluorophenyl]amino]carbonyl]amino]phenoxy]-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
In dichloromethane for 48h;96%
In acetone at 20 - 40℃;
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-(trifluoromethyl)benzoic acid
1737-36-6

4-chloro-3-(trifluoromethyl)benzoic acid

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

4-(4-(4-chloro-3-(trifluoromethyl)phenylamido)phenoxy)-N-methylpyridine-2-carboxamide

4-(4-(4-chloro-3-(trifluoromethyl)phenylamido)phenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid; 1,1'-carbonyldiimidazole In tetrahydrofuran at 45℃; for 3h; Inert atmosphere; Enzymatic reaction;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In tetrahydrofuran at 20℃; for 2h;
96%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene
69922-27-6

1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene

4-(4-(3-(2-fluoro-5-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpyridine-2-carboxamide
847054-10-8

4-(4-(3-(2-fluoro-5-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
In dichloromethane for 72h;96%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1-Fluoro-2-isocyanato-benzene
16744-98-2

1-Fluoro-2-isocyanato-benzene

4-(4-(3-(2-fluorophenyl)ureido)phenoxy)-N-methylpicolinamide

4-(4-(3-(2-fluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
In dichloromethane for 48h;96%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide
1187086-96-9

N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
In chlorobenzene at 70 - 75℃; for 0.25h; Product distribution / selectivity;95%
In ethyl acetate at 20 - 50℃; for 2.75h;77%
With potassium carbonate In dichloromethane for 8h; Milling;72%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

p-trifluoromethyl-phenylisocyanate
1548-13-6

p-trifluoromethyl-phenylisocyanate

N-methyl-4-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenoxy)pyridine-2-carboxamide

N-methyl-4-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenoxy)pyridine-2-carboxamide

Conditions
ConditionsYield
In dichloromethane for 48h;95%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

3-(Trifluoromethyl)benzoyl chloride
2251-65-2

3-(Trifluoromethyl)benzoyl chloride

N-methyl-4-(4-(3-(trifluoromethyl)benzamido)phenoxy)picolinamide

N-methyl-4-(4-(3-(trifluoromethyl)benzamido)phenoxy)picolinamide

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 2h;95%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 3-(Trifluoromethyl)benzoyl chloride With pyridine In dichloromethane for 14h; Inert atmosphere;
Stage #2: With pyridine
74%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

2,5-difluorophenyl isocyanate
39718-32-6

2,5-difluorophenyl isocyanate

4-(4-(3-(2,5-difluorophenyl)ureido)phenoxy)-N-methylpicolinamide

4-(4-(3-(2,5-difluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
In dichloromethane for 24h;94%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-trifluoromethyl-phenyl acetyl chloride
329-15-7

4-trifluoromethyl-phenyl acetyl chloride

N-methyl-4-(4-(4-(trifluoromethyl)benzamido)phenoxy)picolinamide
1125780-43-9

N-methyl-4-(4-(4-(trifluoromethyl)benzamido)phenoxy)picolinamide

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 2h;93.2%
With pyridine In tetrahydrofuran at 20℃; for 2h;
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

2,6-difluorophenyl isocyanate

2,6-difluorophenyl isocyanate

4-(4-(3-(2,6-difluorophenyl)ureido)phenoxy)-N-methylpicolinamide

4-(4-(3-(2,6-difluorophenyl)ureido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
In dichloromethane for 48h;93%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1-isothiocyanato-4-(methylthio)benzene
15863-41-9

1-isothiocyanato-4-(methylthio)benzene

N-methyl-4-(4-(3-(4-(methylthio)phenyl)thioureido)phenoxy)picolinamide

N-methyl-4-(4-(3-(4-(methylthio)phenyl)thioureido)phenoxy)picolinamide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;93%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-(trifluoromethyl)benzoic acid
1737-36-6

4-chloro-3-(trifluoromethyl)benzoic acid

2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid; 2,2,2,-trichloroethoxycarbonyl azide With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Curtius Rearrangement; Inert atmosphere;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;
93%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-fluorophenyl isothiocyanate
1544-68-9

4-fluorophenyl isothiocyanate

4-(4-(3-(4-fluorophenyl)thioureido)phenoxy)-N-methylpicolinamide
1229611-42-0

4-(4-(3-(4-fluorophenyl)thioureido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;92%
In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;70.3%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

3-nitrophenyl isothiocyanate
3529-82-6

3-nitrophenyl isothiocyanate

N-methyl-4-(4-(3-(3-nitrophenyl)thioureido)phenoxy)picolinamide

N-methyl-4-(4-(3-(3-nitrophenyl)thioureido)phenoxy)picolinamide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;92%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

3-ethoxycarbonylphenyl isothiocyanate
3137-84-6

3-ethoxycarbonylphenyl isothiocyanate

ethyl 3-(3-(4-((2-(methylcarbamoyl)pyridin-4-yl)oxy)phenyl)thioureido)benzoate

ethyl 3-(3-(4-((2-(methylcarbamoyl)pyridin-4-yl)oxy)phenyl)thioureido)benzoate

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;92%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-(tert-butylbenzyl)isothiocyanate
19241-24-8

4-(tert-butylbenzyl)isothiocyanate

4-(4-(3-(4-(tert-butyl)phenyl)thioureido)phenoxy)-N-methylpicolinamide

4-(4-(3-(4-(tert-butyl)phenyl)thioureido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;92%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

2-trifluoromethylbenzoyl chloride
312-94-7

2-trifluoromethylbenzoyl chloride

N-methyl-4-(4-(2-(trifluoromethyl)benzamido)phenoxy)picolinamide

N-methyl-4-(4-(2-(trifluoromethyl)benzamido)phenoxy)picolinamide

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 2h;92%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 16h; Inert atmosphere;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane Inert atmosphere;
91%
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 25 - 35℃; for 18h;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane at 25 - 35℃; for 48.75h;
90 g
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

N-methyl-4-(4-(3-phenylthioureido)phenoxy)picolinamide

N-methyl-4-(4-(3-phenylthioureido)phenoxy)picolinamide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;91%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-Bromophenyl isothiocyanate
1985-12-2

4-Bromophenyl isothiocyanate

4-(4-(3-(4-bromophenyl)thioureido)phenoxy)-N-methylpicolinamide

4-(4-(3-(4-bromophenyl)thioureido)phenoxy)-N-methylpicolinamide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;91%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-bromo-3-(trifluoromethyl)phenyl isocyanate
41513-02-4

4-bromo-3-(trifluoromethyl)phenyl isocyanate

4-{4-[({[4-bromo-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methyl-2-pyridine carboxamide

4-{4-[({[4-bromo-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methyl-2-pyridine carboxamide

Conditions
ConditionsYield
In dichloromethane90%
In dichloromethane90%
In dichloromethane90%
In dichloromethane90%
In dichloromethane at 0 - 20℃; for 16h;90%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4‐(4‐aminophenoxy)‐2‐pyridine carboxylic acid
1012058-77-3

4‐(4‐aminophenoxy)‐2‐pyridine carboxylic acid

Conditions
ConditionsYield
Reflux; Alkaline conditions;90%
With potassium carbonate In water at 100℃; for 2h;90%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide With potassium hydroxide; water at 100℃; for 2h;
Stage #2: With water pH=5;
80%
With water; potassium hydroxide at 100℃;18.9 g

284462-37-9Relevant articles and documents

LEADOPT: An automatic tool for structure-based lead optimization, and its application in structural optimizations of VEGFR2 and SYK inhibitors

Li, Guo-Bo,Ji, Sen,Yang, Ling-Ling,Zhang, Rong-Jie,Chen, Kai,Zhong, Lei,Ma, Shuang,Yang, Sheng-Yong

, p. 523 - 538 (2015)

Lead optimization is one of the key steps in drug discovery, and currently it is carried out mostly based on experiences of medicinal chemists, which often suffers from low efficiency. In silico methods are thought to be useful in improving the efficiency of lead optimization. Here we describe a new in silico automatic tool for structure-based lead optimization, termed LEADOPT. The structural modifications in LEADOPT mainly include two operations: fragment growing and fragment replacing, which are restricted to carry out in the active pocket of target protein with the core scaffold structure of ligand kept unchanged. The bioactivity of the newly generated molecules is estimated by ligand efficiency rather than a commonly used scoring function. Twelve important pharmacokinetic and toxic properties are evaluated using SCADMET, a program for the prediction of pharmacokinetic and toxic properties. LEADOPT was first evaluated using two retrospective cases, in which it showed a very good performance. LEADOPT was then applied to the structural optimizations of the VEGFR2 inhibitor, sorafenib, and the SYK inhibitor, R406. Though just several compounds were synthesized, we have obtained some compounds that are more potent than sorafenib and R406 in enzymatic and functional assays. All of these have validated, at least to some extent, the effectiveness of LEADOPT.

Sorafenib sulfydryl derivative and application thereof

-

Paragraph 0019-0021, (2021/04/10)

The invention belongs to the field of medicine, and relates to a sorafenib sulfhydryl derivative and application thereof, in particular to a sorafenib sulfhydryl derivative and application thereof in preparation of an anti-tumor drug targeted delivery carrier. The structure of the sorafenib sulfhydryl derivative is shown as the following formula, a sulfhydryl functional group is introduced into pyridine-2-formamide of an anti-tumor small-molecule targeted drug sorafenib, and sorafenib can be coupled to free amino of polypeptide through proper linker molecules by utilizing the sulfhydryl functional group, so that a sorafenib polypeptide conjugate is constructed, the conjugate can give play to the targeting effect and tumor inhibition effect of sorafenib at the same time, and can be used as a targeting delivery carrier of antitumor drugs.

Design, synthesis, docking, molecular dynamics and bioevaluation studies on novel N-methylpicolinamide and thienopyrimidine derivatives with inhibiting NF-κB and TAK1 activities: Cheminformatics tools RDKit applied in drug design

Tan, Ninghua,Wang, Linxiao,Wang, Zhe,Zhang, Qian,Zhu, Wufu

, (2021/07/09)

Using cheminformatics tools RDKit and literature investigation, four series of 24 thienopyrimidine/N-methylpicolinamide derivatives substituted with pyrimidine were designed, synthesized and evaluated for activities against three cancer cell lines (MDA-MB-231, HCT116 and A549), TAK1 kinase and NF-κB signaling pathway. Almost all compounds showed selectivity toward the A549 cell lines and the most promising compound 38 could inhibit TAK1 kinase and NF-κB signaling pathway with the IC50 values of 0.58 and 0.84 μM. Moreover, 38 can induce cell cycle arrest of A549 cells at the G2/M checkpoint with 30.57% and induce apoptosis (34.94%) in a concentration-dependent manner. And western blot showed that compound 38 could inhibit TNF-α-induced IκBα phosphorylation, IκBα degradation, p65 phosphorylation and TAK1 phosphorylation, and reduce the expression of p65. What's more, the studies of docking, molecular dynamics, MM/PBSA and frequency analysis theoretically supported the conclusions of the bioevaluation.

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