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42288-26-6

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42288-26-6 Usage

Description

Dabigatran etexilate is a novel synthetic direct thrombin inhibitor, a prodrug of dabigatran, a non-peptide thrombin inhibitor. Dabigatran etexilate intermediate II is an impurity produced during the preparation of dabigatran etexilate.

Physical properties

N-(4-Cyanophenyl)glycine is a off-white Solid.

Uses

N-(4-Cyanophenyl)-glycine (cas# 42288-26-6) is a compound useful in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 42288-26-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,2,8 and 8 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 42288-26:
(7*4)+(6*2)+(5*2)+(4*8)+(3*8)+(2*2)+(1*6)=116
116 % 10 = 6
So 42288-26-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H8N2O2/c10-5-7-1-3-8(4-2-7)11-6-9(12)13/h1-4,11H,6H2,(H,12,13)

42288-26-6SDS

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 2-((4-Cyanophenyl)amino)acetic acid

1.2 Other means of identification

Product number -
Other names N-(4-Cyanophenyl)-glycine

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:42288-26-6 SDS

42288-26-6Synthetic route

bromoacetic acid
79-08-3

bromoacetic acid

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
In water at 100 - 110℃; for 3h;88%
In water at 100℃; for 16h;
In water at 20 - 100℃; for 16.4h;
In water at 100℃; for 5h;
In water at 100℃;
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

glycine
56-40-6

glycine

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid In water; dimethyl sulfoxide at 25℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;88%
sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
In water for 6.5h; Product distribution / selectivity; Reflux;73.2%
With water at 0℃; Product distribution / selectivity; Reflux;73.2%
Stage #1: sodium monochloroacetic acid; 4-Aminobenzonitrile With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 90 - 95℃; for 24h;
Stage #2: With ammonia In water at 20 - 30℃; for 0.333333h; pH=7.5;
Stage #3: With hydrogenchloride In water at 20 - 30℃; for 3h; pH=2.5; Product distribution / selectivity;
With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 90 - 95℃; for 24h;131 g
With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 85 - 90℃; for 24h;120 g
chloroacetic acid
79-11-8

chloroacetic acid

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
In water Reflux;73%
In water Heating / reflux;58%
In water Reflux;47%
With water
Glyoxilic acid
298-12-4

Glyoxilic acid

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
With sodium cyanoborohydride for 2h; Milling;56%
(4-cyanophenylamino)-acetic acid tert-butyl ester
144656-11-1

(4-cyanophenylamino)-acetic acid tert-butyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid
With trifluoroacetic acid In dichloromethane for 24h; Ambient temperature;
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / dimethylformamide / 16 h / 80 °C
2: TFA / CH2Cl2; various solvent(s) / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: K2CO3
2: TFA, anisole
View Scheme
(R)-2-(4-methylamino-3-amino-phenyl)-2-tert.butyloxycarbonylamino-1-pyrrolidino-propanone
253796-98-4

(R)-2-(4-methylamino-3-amino-phenyl)-2-tert.butyloxycarbonylamino-1-pyrrolidino-propanone

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

(R)-2-(4-cyanophenylaminomethyl)-1-methyl-5-[1-(N-tert-butyloxycarbonylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole

(R)-2-(4-cyanophenylaminomethyl)-1-methyl-5-[1-(N-tert-butyloxycarbonylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole

Conditions
ConditionsYield
In tetrahydrofuran; acetic acid100%
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate
212322-56-0

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate
948551-71-1

3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 5℃; for 6h; Large scale;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In dichloromethane at 20℃; for 24h; Solvent; Reagent/catalyst; Large scale;
99.3%
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran at 20℃;
93.8%
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0 - 10℃; for 0.5h; Large scale;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran at 20 - 25℃; for 6h; Large scale;
84.33%
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran for 24h; Heating; Further stages.;
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

(piperidin-4-yl)carbamic acid tert-butyl ester
73874-95-0

(piperidin-4-yl)carbamic acid tert-butyl ester

tert-butyl N-[1-[2-(4-cyanoanilino)acetyl]-4-piperidyl]carbamate

tert-butyl N-[1-[2-(4-cyanoanilino)acetyl]-4-piperidyl]carbamate

Conditions
ConditionsYield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;99%
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

tert-butyl N-(4-piperidinylmethyl)carbamate
135632-53-0

tert-butyl N-(4-piperidinylmethyl)carbamate

tert-butyl N-[[1-[2-(4-cyanoanilino)acetyl]-4-piperidyl]methyl]carbamate

tert-butyl N-[[1-[2-(4-cyanoanilino)acetyl]-4-piperidyl]methyl]carbamate

Conditions
ConditionsYield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;98%
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-({3-[2-(4-Cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-phenyl-amino)-propionic acid methyl ester
1315605-52-7

3-({3-[2-(4-Cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-phenyl-amino)-propionic acid methyl ester

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In tetrahydrofuran97%
4-[1-(pyrrolidin-1-yl-carbonyl)cyclopropyl]-2-nitro-N-methylaniline
253431-25-3

4-[1-(pyrrolidin-1-yl-carbonyl)cyclopropyl]-2-nitro-N-methylaniline

4-[1-(N-(3-ethoxycarbonyl-propionyl)-N-cyclopentyl-amino)cyclopropyl]-2-amino-N-methyl-aniline, O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

4-[1-(N-(3-ethoxycarbonyl-propionyl)-N-cyclopentyl-amino)cyclopropyl]-2-amino-N-methyl-aniline, O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

4-[1-(N-(3-ethoxycarbonylpropionyl)-N-cyclopentyl-amino)-cyclopropyl]-2-(4-cyanophenyl)-aminomethylcarbonylamino-N-methyl-aniline

4-[1-(N-(3-ethoxycarbonylpropionyl)-N-cyclopentyl-amino)-cyclopropyl]-2-(4-cyanophenyl)-aminomethylcarbonylamino-N-methyl-aniline

Conditions
ConditionsYield
With triethylamine In N-methyl-acetamide96%
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate
212322-56-0

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
211915-84-3

3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine; ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate With 1,1'-carbonyldiimidazole In Isopropyl acetate at 20℃; for 4h;
Stage #2: With acetic acid In Isopropyl acetate for 2h; Reflux;
95%
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In toluene at 50℃;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In toluene at 20 - 25℃; Temperature;
93.97%
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 3℃; for 1h;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In N,N-dimethyl-formamide at 20℃; for 6h; Temperature; Further stages;
91.1%
3-[(3-amino-4-butyl aminobenzoyl)(3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester

3-[(3-amino-4-butyl aminobenzoyl)(3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{1-butyl-2-[(4-cyanophenylamino)methyl]-1H-benzoimidazole-5-carbonyl} (3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester

3-[{1-butyl-2-[(4-cyanophenylamino)methyl]-1H-benzoimidazole-5-carbonyl} (3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-butyl aminobenzoyl)(3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester In tetrahydrofuran at 20℃; for 4h;
Stage #3: With acetic acid for 3h; Reflux;
95%
3-[(3-amino-4-ethylamino-benzoyl)-(3,5-difluorophenyl)-amino]-propionic acid ethyl ester

3-[(3-amino-4-ethylamino-benzoyl)-(3,5-difluorophenyl)-amino]-propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-N-(3,5-difluorophenyl)-1-ethyl-1H-benzo[d]imidazole-5-carboxamido)propanoate

ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-N-(3,5-difluorophenyl)-1-ethyl-1H-benzo[d]imidazole-5-carboxamido)propanoate

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.583333h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylamino-benzoyl)-(3,5-difluorophenyl)-amino]-propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;
Stage #3: With acetic acid at 120℃; for 2 - 3h;
93%
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

acetic acid
64-19-7

acetic acid

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate
212322-56-0

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide acetate salt
1188417-09-5

1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide acetate salt

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.666667h; Inert atmosphere; Reflux;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran for 5h; Inert atmosphere; Reflux;
Stage #3: acetic acid In tetrahydrofuran for 1h; Reflux;
92%
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate
212322-56-0

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide p-toluenesulfonate

1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide p-toluenesulfonate

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With pivaloyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 5℃;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran at 0 - 5℃; for 0.0833333h;
Stage #3: toluene-4-sulfonic acid Further stages;
89.59%
Stage #1: (4-cyanophenyl)glycine With Imidazole hydrochloride; 1,1'-carbonyldiimidazole In dichloromethane at 35 - 40℃; for 1h; Inert atmosphere;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In dichloromethane for 1h; Inert atmosphere; Reflux;
Stage #3: toluene-4-sulfonic acid In acetic acid butyl ester at 85 - 90℃; for 1h; Solvent; Inert atmosphere;
15.8 g
ethyl 3-(3-amino-4-(ethylamino)-N-(2-fluorophenyl)-benzamido)propanoate

ethyl 3-(3-amino-4-(ethylamino)-N-(2-fluorophenyl)-benzamido)propanoate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-ethyl-N-(2-fluorophenyl)-1H-benzo[d]imidazole-5-carboxamido)-propanoate

ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-ethyl-N-(2-fluorophenyl)-1H-benzo[d]imidazole-5-carboxamido)-propanoate

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.583333h; Cooling with ice;
Stage #2: ethyl 3-(3-amino-4-(ethylamino)-N-(2-fluorophenyl)-benzamido)propanoate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;
Stage #3: With acetic acid at 120℃; for 2 - 3h;
89%
(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[(3-amino-4-methylaminobenzoyl)-(2-methoxyphenyl)amino]-propionic acid ethyl ester

3-[(3-amino-4-methylaminobenzoyl)-(2-methoxyphenyl)amino]-propionic acid ethyl ester

3-({2-[(4-cyanophenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-(2-methoxyphenyl)amino)propionic acid ethyl ester

3-({2-[(4-cyanophenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-(2-methoxyphenyl)amino)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-methylaminobenzoyl)-(2-methoxyphenyl)amino]-propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 5h;
89%
ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,3-dimethylphenyl)-5-oxopentanoate

ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,3-dimethylphenyl)-5-oxopentanoate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,3-dimethylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,3-dimethylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,3-dimethylphenyl)-5-oxopentanoate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;
87.6%
3-[(3-amino-4-ethylaminobenzoyl)-(2,3-dimethylphenyl)amino]propionic acid ethyl ester

3-[(3-amino-4-ethylaminobenzoyl)-(2,3-dimethylphenyl)amino]propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,3-dimethylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,3-dimethylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylaminobenzoyl)-(2,3-dimethylphenyl)amino]propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 10h;
87.6%
3-[(3-amino-4-ethylaminobenzoyl)-(4-fluoro-3-methylphenyl)amino]propionic acid ethyl ester

3-[(3-amino-4-ethylaminobenzoyl)-(4-fluoro-3-methylphenyl)amino]propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(4-fluoro-3-methylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(4-fluoro-3-methylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylaminobenzoyl)-(4-fluoro-3-methylphenyl)amino]propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 10h;
87.6%
tert-butyl N-[(4-fluoropiperidin-4-yl)methyl]carbamate
871022-62-7

tert-butyl N-[(4-fluoropiperidin-4-yl)methyl]carbamate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

tert-butyl N-[[1-[2-(4-cyanoanilino)acetyl]-4-fluoro-4-piperidyl]methyl]carbamate

tert-butyl N-[[1-[2-(4-cyanoanilino)acetyl]-4-fluoro-4-piperidyl]methyl]carbamate

Conditions
ConditionsYield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;87%
3-[(3-amino-4-ethylamino-benzoyl)-(3,5-dimethylphenyl)-amino]-propionic acid ethyl ester

3-[(3-amino-4-ethylamino-benzoyl)-(3,5-dimethylphenyl)-amino]-propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(3,5-dimethylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(3,5-dimethylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylamino-benzoyl)-(3,5-dimethylphenyl)-amino]-propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 10h;
86.1%
3-[(3-chloro-4-methyl amino benzoyl)(3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester

3-[(3-chloro-4-methyl amino benzoyl)(3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-((3-chloro-4-fluorophenyl){2-[(4-cyanophenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}amino)propionic acid ethyl ester

3-((3-chloro-4-fluorophenyl){2-[(4-cyanophenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}amino)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: 3-[(3-chloro-4-methyl amino benzoyl)(3-chloro-4-fluorophenyl)amino]propionic acid ethyl ester In tetrahydrofuran at 20℃; for 4h;
Stage #3: With acetic acid for 3h; Reflux;
86%
ethyl 3-amino-4-(methylamino)benzoate
66315-23-9

ethyl 3-amino-4-(methylamino)benzoate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

C19H20N4O3

C19H20N4O3

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 10 - 20℃;86%
3-[(3-amino-4-ethylaminobenzoyl)-(3-fluoro-4-methylphenyl)amino]propionic acid ethyl ester

3-[(3-amino-4-ethylaminobenzoyl)-(3-fluoro-4-methylphenyl)amino]propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(3-fluoro-4-methylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(3-fluoro-4-methylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylaminobenzoyl)-(3-fluoro-4-methylphenyl)amino]propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 10h;
85.8%
ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,4-dimethylphenyl)-5-oxopentanoate

ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,4-dimethylphenyl)-5-oxopentanoate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,4-dimethylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,4-dimethylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,4-dimethylphenyl)-5-oxopentanoate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;
85.5%
3-[(3-amino-4-ethylamino-benzoyl)-(3,4-dimethylphenyl)-amino]-propionic acid ethyl ester

3-[(3-amino-4-ethylamino-benzoyl)-(3,4-dimethylphenyl)-amino]-propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}-(3,4-dimethyl-phenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}-(3,4-dimethyl-phenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylamino-benzoyl)-(3,4-dimethylphenyl)-amino]-propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 10h;
85.5%
3-[(3-amino-4-ethylamino-benzoyl)-(2,4-dimethylphenyl)-amino]-propionic acid ethyl ester

3-[(3-amino-4-ethylamino-benzoyl)-(2,4-dimethylphenyl)-amino]-propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,4-dimethylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,4-dimethylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylamino-benzoyl)-(2,4-dimethylphenyl)-amino]-propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 10h;
85.4%
methanesulfonic acid
75-75-2

methanesulfonic acid

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate
212322-56-0

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate mesylate

ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate mesylate

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran at 30 - 35℃;
Stage #3: methanesulfonic acid Further stages;
85%
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25 - 35℃; for 3h;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran at 25 - 35℃; for 24h;
Stage #3: methanesulfonic acid In acetone at 0 - 10℃; for 3h; Concentration; Temperature;
220 g
3-[(3-amino-4-ethylaminobenzoyl)(2,5-dimethyl-phenyl)amino]propionic acid ethyl ester

3-[(3-amino-4-ethylaminobenzoyl)(2,5-dimethyl-phenyl)amino]propionic acid ethyl ester

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,5-dimethylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,5-dimethylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 3-[(3-amino-4-ethylaminobenzoyl)(2,5-dimethyl-phenyl)amino]propionic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 10h;
84.5%
ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,5-dimethylphenyl)-5-oxopentanoate

ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,5-dimethylphenyl)-5-oxopentanoate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,5-dimethylphenyl)amino]propionic acid ethyl ester

3-[{2-[(4-cyanophenylamino)methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}(2,5-dimethylphenyl)amino]propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(2,5-dimethylphenyl)-5-oxopentanoate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;
84.2%
ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(3-methylphenyl)-5-oxopentanoate

ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(3-methylphenyl)-5-oxopentanoate

(4-cyanophenyl)glycine
42288-26-6

(4-cyanophenyl)glycine

ethyl 3-{[(2-{[(4-cyanophenyl)amino]methyl}-1-ethyl-1H-benzimidazol-5-yl)carbonyl](3-methylphenyl)amino}propanoate

ethyl 3-{[(2-{[(4-cyanophenyl)amino]methyl}-1-ethyl-1H-benzimidazol-5-yl)carbonyl](3-methylphenyl)amino}propanoate

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: ethyl 5-[3-amino-4-(ethylamino)phenyl]-4-(3-methylphenyl)-5-oxopentanoate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;
83.7%

42288-26-6Downstream Products

42288-26-6Relevant articles and documents

Mechanosynthesis of sydnone-containing coordination complexes

Pétry, Nicolas,Vanderbeeken, Thibaut,Malher, Astrid,Bringer, Yoan,Retailleau, Pascal,Bantreil, Xavier,Lamaty, Frédéric

supporting information, p. 9495 - 9498 (2019/08/15)

N-Phenyl-4-(2-pyridinyl) sydnone was shown to act as a four-electron donor N,O-ligand in unprecedented coordination complexes featuring three different metallic centers (Co, Cu, and Zn). Starting with various anilines, the use of a ball-mill efficiently enabled the synthesis of N-arylglycines, subsequent nitrosylation and cyclization into sydnones, and further metalation.

Multi-substituted 4-methyl ester derivative of amino benzonitrile trunk and its preparation and use

-

Paragraph 0096; 0102-0104, (2018/01/19)

The invention provides new ester derivatives with a general formula (I) shown in the specification of multi-substituted 4-methylamino-benzamidine or pharmaceutically acceptable salts, wherein A1, A2, A3 and A4 in the formula are as defined in the specification. The compounds have an anticoagulant effect and can be used for preparing medicaments for preventing and treating thromboembolic diseases.

N-(1-Oxy-2-picolyl)oxalamic Acid as an Efficient Ligand for Copper-Catalyzed Amination of Aryl Iodides at Room Temperature

Wang, Yongbin,Ling, Jing,Zhang, Yu,Zhang, Ao,Yao, Qizheng

, p. 4153 - 4161 (2015/07/01)

N-(1-Oxy-pyridin-2-ylmethyl)oxalamic acid was identified as efficient ligand for CuI-catalyzed amination of aryl halides at room temperature. In our catalytic system, N-arylation of cyclic secondary amines, primary amines, amino acids, and ammonia proceeded with moderate to excellent yields and high functional group tolerance.

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