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211915-84-3
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Basic Information
CAS No.: 211915-84-3
Name: 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester
Molecular Structure:
Molecular Structure of 211915-84-3 (3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester)
Formula: C27H26N6O3
Molecular Weight: 482.542
Synonyms: Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido;
EINECS: 1592732-453-0
Density: 1.255 g/cm3
Boiling Point: 756.382 °C at 760 mmHg
Flash Point: 411.245 °C
PSA: 113.14000
LogP: 4.12508
Related products
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
ConditionsYield
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
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%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
Raw Materials
429659-01-8
42288-26-6
82357-48-0
212322-56-0
41263-74-5
873-74-5
96-99-1
Downstream Products
872728-81-9
211915-06-9
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Chemistry

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

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 .