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

Name
3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester
EINECS 1592732-453-0
CAS No. 211915-84-3
Article Data29
CAS DataBase
Density 1.255 g/cm³
Solubility
Melting Point
Formula C₂₇H₂₆N₆O₃
Boiling Point 756.382 °C at 760 mmHg
Molecular Weight 482.542
Flash Point 411.245 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido;
PSA 113.14000
LogP 4.12508

Synthetic route

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

: 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

Conditions	Yield
With ammonium hydroxide In dichloromethane; water pH=8 - 10;	95.5%

: 42288-26-6
(4-cyanophenyl)glycine

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

: 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

Conditions	Yield
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%

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

: 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

Conditions	Yield
With acetic acid at 110℃; for 2h; Large scale;	92%
With acetic acid In acetic acid butyl ester at 85 - 90℃;	90.8%
Stage #1: 3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate With acetic acid In dichloromethane at 80 - 85℃; for 10h; Large scale; Stage #2: With ammonia In dichloromethane pH=9; Reagent/catalyst; Solvent; Large scale;	83.3%
With acetic acid for 1h; Heating;
In toluene Reflux;	120 g

: isopropyl 2‑(4‑cyanophenylamino)acetate

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

: 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

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 10 - 35℃;	82%

: ethyl 2-((4-cyanophenyl)amino)acetate

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

: 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

Conditions	Yield
In propionic acid at 130℃; for 12h; Solvent; Temperature;	81%

: 2-(4-cyanophenylamino)acetamide

: C19H23N3O4

: 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

Conditions	Yield
With acetic acid; 1,1'-carbonyldiimidazole In ethyl acetate at 50℃; for 6h; Concentration;	47.7%

: 82357-48-0
4-methylamino-3-nitro-benzoic acid chloride

: 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

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Et3N / tetrahydrofuran / 20 °C 2.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 3.1: CDI / tetrahydrofuran / 50 °C 3.2: tetrahydrofuran / 24 h / Heating 4.1: glacial acetic acid / 1 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran; dichloromethane / 2 h / 40 °C 2.1: palladium on activated charcoal; hydrogen / water; ethanol / 50 °C / Autoclave 3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.67 h / Inert atmosphere; Reflux 3.2: 7 h / Inert atmosphere; Reflux 3.3: 3 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0 - 10 °C 1.2: 0 - 30 °C 2.1: hydrogen / ethyl acetate / 60 - 65 °C / 7500.75 Torr 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 5 °C 3.2: 0.08 h / 0 - 5 °C 4.1: ammonium hydroxide / water; dichloromethane / pH 8 - 10 View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 12 h / 20 °C 2.1: palladium 10% on activated carbon / 20 h / 22801.5 Torr 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 3.2: 20 °C View Scheme

: 41263-74-5
4-(methylamino)-3-nitrobenzoic acid

: 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

Conditions	Yield
Multi-step reaction with 5 steps 1.1: SOCl2 / dimethylformamide / 0.5 h / Heating 2.1: Et3N / tetrahydrofuran / 20 °C 3.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 4.1: CDI / tetrahydrofuran / 50 °C 4.2: tetrahydrofuran / 24 h / Heating 5.1: glacial acetic acid / 1 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / tetrahydrofuran / 0.67 - 0.75 h / Reflux; Inert atmosphere 2.1: triethylamine / tetrahydrofuran; dichloromethane / 2 h / 40 °C 3.1: palladium on activated charcoal; hydrogen / water; ethanol / 50 °C / Autoclave 4.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.67 h / Inert atmosphere; Reflux 4.2: 7 h / Inert atmosphere; Reflux 4.3: 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 1.25 h / 25 - 80 °C 1.2: 1 h 2.1: palladium on activated charcoal / ethyl acetate / 0.33 h / 25 - 55 °C / High pressure 3.1: 1,1'-carbonyldiimidazole / toluene / 2 h / 55 - 60 °C 3.2: 6 h / 60 - 100 °C View Scheme

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

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CDI / tetrahydrofuran / 50 °C 1.2: tetrahydrofuran / 24 h / Heating 2.1: glacial acetic acid / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 5 °C 1.2: 0.08 h / 0 - 5 °C 2.1: ammonium hydroxide / water; dichloromethane / pH 8 - 10 View Scheme
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.5 h / 20 °C 1.2: 20 °C 2.1: acetic acid / acetic acid butyl ester / 85 - 90 °C View Scheme
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 6 h / 0 - 5 °C / Large scale 1.2: 24 h / 20 °C / Large scale 2.1: acetic acid / dichloromethane / 10 h / 80 - 85 °C / Large scale 2.2: pH 9 / Large scale View Scheme

: 429659-01-8
ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 2.1: CDI / tetrahydrofuran / 50 °C 2.2: tetrahydrofuran / 24 h / Heating 3.1: glacial acetic acid / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: palladium on activated charcoal / ethyl acetate / 0.33 h / 25 - 55 °C / High pressure 2.1: 1,1'-carbonyldiimidazole / toluene / 2 h / 55 - 60 °C 2.2: 6 h / 60 - 100 °C View Scheme
Multi-step reaction with 2 steps 1.1: palladium on activated charcoal / ethyl acetate / 25 - 55 °C 2.1: 1,1'-carbonyldiimidazole / toluene / 25 - 60 °C 2.2: 6 h / 60 - 100 °C View Scheme

: 873-74-5
4-Aminobenzonitrile

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium iodide; sodium hydrogencarbonate; tetrabutylammomium bromide / water / 24 h / 90 - 95 °C 1.2: 0.33 h / 20 - 30 °C / pH 7.5 1.3: 3 h / 20 - 30 °C / pH 2.5 2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 50 - 55 °C 2.2: 50 h / 50 - 65 °C View Scheme
Multi-step reaction with 2 steps 1.1: water / 16 h / 100 °C 2.1: 1,1'-carbonyldiimidazole / toluene / 2 h / 55 - 60 °C 2.2: 6 h / 60 - 100 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium iodide; tetrabutylammomium bromide; sodium hydrogencarbonate / water / 24 h / 90 - 95 °C 2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 3 h / 50 - 55 °C 2.2: 52 h / 50 - 65 °C 2.3: 5 h / 95 - 100 °C View Scheme

: ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride hemisulfate

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium on activated charcoal; hydrogen / water; ethanol / 50 °C / Autoclave 2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.67 h / Inert atmosphere; Reflux 2.2: 7 h / Inert atmosphere; Reflux 2.3: 3 h / Reflux View Scheme

: 103041-38-9
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

: 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

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0 - 10 °C 1.2: 0 - 30 °C 2.1: hydrogen / ethyl acetate / 60 - 65 °C / 7500.75 Torr 3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 5 °C 3.2: 0.08 h / 0 - 5 °C 4.1: ammonium hydroxide / water; dichloromethane / pH 8 - 10 View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 12 h / 20 °C 2.1: palladium 10% on activated carbon / 20 h / 22801.5 Torr 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 3.2: 20 °C View Scheme

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

: 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

Conditions	Yield
With ammonium hydroxide In dichloromethane; water at 25 - 35℃; for 0.166667h; pH=9.5;	55 g

: 42288-26-6
(4-cyanophenyl)glycine

: 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

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dichloromethane / Reflux 2.1: dichloromethane / 4 h / Reflux 3.1: toluene / Dean-Stark; Reflux 3.2: 0.5 h / Reflux 4.1: ammonium hydroxide / dichloromethane; water / 0.17 h / 25 - 35 °C / pH 9.5 View Scheme
Multi-step reaction with 3 steps 1: dichloromethane / 20 - 25 °C / Inert atmosphere 2: toluene / 3 h / 50 °C 3: toluene / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.5 h / 20 °C 1.2: 20 °C 2.1: acetic acid / acetic acid butyl ester / 85 - 90 °C View Scheme
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 6 h / 0 - 5 °C / Large scale 1.2: 24 h / 20 °C / Large scale 2.1: acetic acid / dichloromethane / 10 h / 80 - 85 °C / Large scale 2.2: pH 9 / Large scale View Scheme

: 4-(2-imidazol-1-yl-2-oxoethylamino)benzonitrile

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane / 4 h / Reflux 2.1: toluene / Dean-Stark; Reflux 2.2: 0.5 h / Reflux 3.1: ammonium hydroxide / dichloromethane; water / 0.17 h / 25 - 35 °C / pH 9.5 View Scheme

: 3-amino-4-[N-[2-(4-cyanophenylamino)acetyl]-N-methylamino]benzoic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene / Dean-Stark; Reflux 1.2: 0.5 h / Reflux 2.1: ammonium hydroxide / dichloromethane; water / 0.17 h / 25 - 35 °C / pH 9.5 View Scheme

: 41608-64-4
methyl 3-methoxy-4-aminobenzoate

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 3.5 h / 0 - 25 °C 2: ethyl acetate / 12 h / 25 °C 3: 1,1'-carbonyldiimidazole; acetic acid / ethyl acetate / 6 h / 50 °C View Scheme

: C27H26N6O6

: 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

Conditions	Yield
With 5% Pd(OH)2/C; hydrogen; acetic acid In ethyl acetate under 750.075 Torr;	14.9 mg

: C27H29N7O4

: 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

Conditions	Yield
With acetic acid for 1.5h; Reflux;

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

: 3-({2-[(4-carbamimidoylphenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol at 35 - 42℃; Stage #2: With ammonium carbonate; ammonia In ethanol at 0 - 32℃;	96.61%
With lithium hexamethyldisilazane In tetrahydrofuran at -5 - 20℃; for 2h; Solvent;	95%
With hydrogenchloride In ethanol at 20℃;	92%

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

: 212322-77-5
3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 2h;	96.1%

: 64-17-5
ethanol

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

: 1354727-65-3
3-({2-[(4-ethoxycarbonimidoylphenylamino)methyl]1-methyl-1H-benzimidazol-5-carbonyl}pyridin-2-yl-amino)ethyl propanoate hydrochloride

Conditions

Conditions	Yield
With trichlorophosphate at 0 - 25℃;	93%
With hydrogenchloride at 10 - 35℃; for 24h;
With hydrogenchloride In chloroform; toluene at 10℃; for 24h; Solvent; Temperature;

: 98-11-3
benzenesulfonic acid

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

: ethyl 3-[[[2-[[(4-amidinophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propanoate benzensulfonate

Conditions

Conditions	Yield
Stage #1: benzenesulfonic acid; 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol; water at -5 - 20℃; for 24h; Stage #2: With ammonia In ethanol; water at 0 - 20℃; for 24h; Temperature; Concentration;	92.6%

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

: 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride salt

Conditions

Conditions	Yield
Stage #1: 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol at 10 - 25℃; Stage #2: With ammonium hydroxide at 0 - 20℃;	81.9%
Stage #1: 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol at 25℃; for 25h; Stage #2: With ammonium hydroxide In ethanol for 6h; pH=8.5 - 9.5;	77%
Stage #1: 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride; propionyl chloride; Ethyl propionate In ethanol; water at 10 - 40℃; for 10h; Pinner Amidine Synthesis; Large scale; Stage #2: With ammonium hydroxide In ethanol; water at 50℃; for 10h; pH=9; Solvent; Reagent/catalyst; Concentration; Large scale;	75.4%

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

: 658078-29-6
C27H29N7O4

Conditions

Conditions	Yield
Stage #1: 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol Stage #2: With hydroxylamine hydrochloride; triethylamine In ethanol	80%

: 60-29-7
diethyl ether

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

: 212322-77-5
3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water	78%

: 104-15-4
toluene-4-sulfonic acid

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

: 872728-85-3
1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt

Conditions

Conditions	Yield
Stage #1: toluene-4-sulfonic acid; 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol at 25 - 30℃; for 20h; Autoclave; Large scale; Stage #2: With ammonia In ethanol at 20 - 30℃; for 2h; Autoclave; Large scale; Stage #3: With sodium hydroxide In ethanol; water at 20℃; for 1h; Autoclave; Large scale;	73.48%
With hydrogenchloride In ethanol at 0 - 17℃; for 18h; Temperature;	26.2 g

Yield

Stage #1: toluene-4-sulfonic acid; 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol at 25 - 30℃; for 20h; Autoclave; Large scale;
Stage #2: With ammonia In ethanol at 20 - 30℃; for 2h; Autoclave; Large scale;
Stage #3: With sodium hydroxide In ethanol; water at 20℃; for 1h; Autoclave; Large scale;

73.48%

With hydrogenchloride In ethanol at 0 - 17℃; for 18h; Temperature;

26.2 g

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

: 658078-29-6
1-methyl-2-[4-(N-hydroxyamidino)-phenylaminomethyl]-benzimidazol-5-yl-carboxylic acid-(N-2-pyridyl-N-2-ethoxycarbonylethyl)-amide

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In dimethyl sulfoxide at 20 - 30℃; for 24h; Solvent; Reagent/catalyst; Temperature;	70%
With hydroxylamine hydrochloride; sodium ethanolate In ethanol at 0 - 58℃; for 24h;

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

: 1-methyl-2-[4-(N-hydroxyamidino)-phenylaminomethyl]-benzimidazol-5-yl-carboxylic acid (N-2-pyridyl-N-2-ethoxycarbonylethyl)-amide

Conditions

Conditions	Yield
Stage #1: 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With hydrogenchloride In ethanol at 0 - 20℃; for 5h; Stage #2: With hydroxylamine hydrochloride; triethylamine In ethanol at 0 - 20℃; for 2h;	61.5%

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

: N-[[2-[[[4-(N'-hydroxycarbamimidoyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridyl)-β-alanine ethyl ester hydrochloride

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In methanol at 50 - 55℃; for 3h; Solvent; Temperature; Reagent/catalyst;	50%

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

: dabigatran

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: HCl / ethanol / 0 °C 1.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 2.1: 91 percent / aq. NaOH / ethanol / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 12 h / 20 °C 1.2: 5 h / 20 °C 2.1: sodium hydroxide; water / ethanol / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water / 18 h / 10 - 15 °C 2.1: acetone / 2 h / 20 °C 3.1: potassium carbonate / water / 20 - 25 °C / pH Ca. 10 3.2: 8 h 4.1: sodium hydroxide / water; ethanol / 6 h View Scheme

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

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: HCl / ethanol / 0 °C 1.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 2.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C 2.2: 51 percent / tetrahydrofuran / 1 h / 20 °C View Scheme

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

: 1046806-03-4
BrH*C27H26N6O3

Conditions

Conditions	Yield
With hydrogen bromide In water; isopropyl alcohol at 7 - 38℃; for 1.33333h; pH=0.6 - 1.3; Industry scale;

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

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: calcium(II) chloride dihydrate / ethanol / 0.33 h 1.2: 13 h / 0 - 30 °C 1.3: 10.5 h / 0 - 35 °C 2.1: ethanol / 6.75 h / 25 - 60 °C 3.1: potassium carbonate / acetonitrile; water / 0.25 h / 12 - 18 °C 3.2: 4.5 h / 12 - 18 °C View Scheme
Multi-step reaction with 3 steps 1.1: calcium(II) chloride dihydrate / ethanol / 0.33 h 1.2: 13 h / 0 - 30 °C 1.3: 10.5 h / 0 - 35 °C 2.1: ethanol / 6.75 h / 25 - 60 °C 3.1: potassium carbonate / acetonitrile; water / 0.25 h / 12 - 18 °C 3.2: 14.42 h / 12 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol; dichloromethane / 6 h / 15 - 30 °C 1.2: 15 - 30 °C 2.1: triethylamine / water; acetonitrile / 15 °C View Scheme

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

: 1-methyl-2-[N-(4-amidinophenyl)-aminomethyl]benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / isopropyl alcohol / 1 h / 0 - 35 °C 2: hydrogenchloride / 24 h / 30 °C 3: ammonium carbonate / ethanol / 20 °C / Inert atmosphere View Scheme
Stage #1: 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester With calcium(II) chloride dihydrate In ethanol for 0.333333h; Stage #2: With hydrogenchloride at 0 - 30℃; for 13h; Stage #3: With ammonium formate; ammonium carbonate at 0 - 35℃; for 10h;	45 g

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

: ethyl N-[(2-[(p-[ethoxyimidoyl]phenyl)amino]methyl)-1-methyl-1H-benzimidazole-5-carbonyl]-N-(2-pyridyl)-3-aminopropionate hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / isopropyl alcohol / 1 h / 0 - 35 °C 2: hydrogenchloride / 24 h / 30 °C View Scheme

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

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / isopropyl alcohol / 1 h / 0 - 35 °C 2: hydrogenchloride / 24 h / 30 °C 3: ammonium carbonate / ethanol / 20 °C / Inert atmosphere 4: triethylamine / acetone / 1.5 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol / 18 h / 0 - 17 °C 2: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 24 h / 20 °C 1.2: 10 - 20 °C 2.1: potassium carbonate / water; acetone / 10 - 25 °C View Scheme
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; triethylamine / dimethyl sulfoxide / 24 h / 20 - 30 °C 2.1: hydrogen; acetic acid / water / 24 h / 55 - 65 °C 2.2: 1 h 3.1: potassium carbonate / water; acetone / 10 - 20 °C View Scheme

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

: ethyl N-[(2-[(p-cyanophenyl)amino]methyl)-1-methyl-1H-benzimidazole-5-carbonyl]-N-(2-pyridyl)-3-aminopropionate hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 0 - 35℃; for 1h;

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

Following is the structure of 1Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido (CAS NO.211915-84-3):

Empirical Formula: C₂₇H₂₆N₆O₃
Molecular Weight: 482.5337
Index of Refraction: 1.64
Molar Refractivity: 138.5 cm³
Molar Volume: 384.44 cm³
Density: 1.255 g/cm³
Flash Point: 411.245 °C
Polarizability: 54.906 10^-24cm³
Surface Tension: 51.091 dyne/cm
Enthalpy of Vaporization: 110.2 kJ/mol
Boiling Point: 756.382 °C at 760 mmHg
SMILES: O=C(OCC)CCN(c1ncccc1)C(=O)c4ccc2c(nc(n2C)CNc3ccc(C#N)cc3)c4
InChI: InChI=1/C27H26N6O3/c1-3-36-26(34)13-15-33(24-6-4-5-14-29-24)27(35)20-9-12-23-22(16-20)31-25(32(23)2)18-30-21-10-7-19(17-28)8-11-21/h4-12,14,16,30H,3,13,15,18H2,1-2H3
InChIKey: OZBOESGNDSVMDK-UHFFFAOYAB

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

Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido , its cas register number 211915-84-3. It also can be called beta-Alanine, N-[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-, ethyl ester .

Product Name

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

Synthetic route

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

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

Related Products

Hot Products