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inquiry3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester CAS No.:211915-84-3 Name: 3-[[[2-[[(4-Cyanophenyl)amino]met
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/228.html Product Name 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol -5-yl]carb
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inquiryProduct Name: 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester Synonyms: 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]
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inquiryDensity: 1.25 ± 0.1 g/cm3 (Predicted) Melting point: 149-151 ° C Boiling point: 756.4 ± 60.0 ° C (Predicted) Flash point: 411.245 ° C Steam pressure: 0mmHg at 25 ° C Solubility: DMSO (Slightly, Sonicated), Methanol (Very
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inquiryName Dabigatran Intermediate 3 CAS 211915-84-3 Other name 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic aci
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inquiry3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
Conditions | Yield |
---|---|
With ammonium hydroxide In dichloromethane; water pH=8 - 10; | 95.5% |
(4-cyanophenyl)glycine
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
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% |
3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
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
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 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
Conditions | Yield |
---|---|
In propionic acid at 130℃; for 12h; Solvent; Temperature; | 81% |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
Conditions | Yield |
---|---|
With acetic acid; 1,1'-carbonyldiimidazole In ethyl acetate at 50℃; for 6h; Concentration; | 47.7% |
4-methylamino-3-nitro-benzoic acid chloride
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
4-(methylamino)-3-nitrobenzoic acid
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
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
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 |
ethyl 3-{[{1-(methylamino)-2-nitrophen-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
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 |
4-Aminobenzonitrile
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide acetate salt
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
Conditions | Yield |
---|---|
With ammonium hydroxide In dichloromethane; water at 25 - 35℃; for 0.166667h; pH=9.5; | 55 g |
(4-cyanophenyl)glycine
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
methyl 3-methoxy-4-aminobenzoate
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
Conditions | Yield |
---|---|
With 5% Pd(OH)2/C; hydrogen; acetic acid In ethyl acetate under 750.075 Torr; | 14.9 mg |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
Conditions | Yield |
---|---|
With acetic acid for 1.5h; Reflux; |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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% |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 2h; | 96.1% |
ethanol
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
3-({2-[(4-ethoxycarbonimidoylphenylamino)methyl]1-methyl-1H-benzimidazol-5-carbonyl}pyridin-2-yl-amino)ethyl propanoate hydrochloride
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; |
benzenesulfonic acid
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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% |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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% |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
C27H29N7O4
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% |
diethyl ether
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water | 78% |
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
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 | 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 |
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 | 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; |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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% |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; triethylamine In methanol at 50 - 55℃; for 3h; Solvent; Temperature; Reagent/catalyst; | 50% |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
dabigatran etexilate
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
BrH*C27H26N6O3
Conditions | Yield |
---|---|
With hydrogen bromide In water; isopropyl alcohol at 7 - 38℃; for 1.33333h; pH=0.6 - 1.3; Industry scale; |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
dabigatran etexilate
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
dabigatran etexilate
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 |
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In isopropyl alcohol at 0 - 35℃; for 1h; |
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