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

Base Information

• Chemical Name: Ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate
• CAS No.: 211915-84-3
• Molecular Formula: C27H26N6O3
• Molecular Weight: 482.542
• UNII: B24J67PN4T
• DSSTox Substance ID: DTXSID90469667
• Nikkaji Number: J3.183.849E
• Wikidata: Q72458766
• Mol file: 211915-84-3.mol

Synonyms:211915-84-3;Ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate;3-[[[2-[[(4-CYANOPHENYL)AMINO]METHYL]-1-METHYL-1H-BENZIMIDAZOL-5-YL]CARBONYL]PYRIDIN-2-YLAMINO]PROPIONIC ACID ETHYL ESTER;ethyl 3-[[2-[(4-cyanoanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate;Dabigatran impurity I;Deacetamidine cyano dabigatran ethyl ester;DeacetamidineCyanoDabigatran-d3EthylEster;Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate;3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionic acid ethyl ester;OZBOESGNDSVMDK-UHFFFAOYSA-N;CID 11627749;Dabigatran Intermediate 3;SCHEMBL505917;B24J67PN4T;OZBOESGNDSVMDK-UHFFFAOYSA-;AMY4165;DTXSID90469667;C27H26N6O3;BCP27981;CS-M2456;MFCD09833627;AKOS015891389;AC-7905;3-({2-[(4-cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl]pyridin-2-ylamino)propion;DS-18531;Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido;Ethyl 3-[[2-[(4-Cyanoanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-(2-pyridyl)amino]propanoate;A4584;FT-0687614;Q-102528;?-Alanine, N-[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-, ethyl ester;1-Methyl-2-[((4-cyanophenyl)amino)methyl]-benzimidazole-5-carboxamide N-(2-pyridyl)-N-(2-(ethoxycarbonyl)ethyl);Deacetamidine Cyano Dabigatran Ethyl Ester;1-methyl-2-[N-(4-cyanophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide;1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide;3-((2-(((4-cyanophenyl)aminomethyl)-1-methyl-1h-benzimidazol-5-yl)carbonyl)pyridin-2-ylamino)propionic acid ethyl ester;3-[[[2-[[(4-Cyanophenyl) amino]methyl] -1-methyl- 1H- benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester;3-[[[2-[[(4-cyanophenyl) amino]methyl]-1-methyl-1h-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester;Ethyl 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionate;ethyl 3-{[(2-{[(4-cyanophenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](pyridin-2-yl)amino}propanoate;Ethyl N-{2-[(4-cyanoanilino)methyl]-1-methyl-1H-benzimidazole-5-carbonyl}-N-pyridin-2-yl-beta-alaninate;Ethyl3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate;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

Chemical Property of Ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate

Chemical Property:

• Boiling Point: 756.382 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 411.245 °C
• PSA: 113.14000
• Density: 1.255 g/cm³
• LogP: 4.12508
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Very Slightly, Sonicated)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 482.20663871
• Heavy Atom Count: 36
• Complexity: 792

Purity/Quality:

≥98.0% ^*data from raw suppliers

DeacetamidineCyanoDabigatranEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCN(C1=CC=CC=N1)C(=O)C2=CC3=C(C=C2)N(C(=N3)CNC4=CC=C(C=C4)C#N)C
• Uses: Nonpeptide thrombin inhibitor intermediate.

Technology Process of Ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate

There total 23 articles about Ethyl 3-(2-(((4-cyanophenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.5%

1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide p-toluenesulfonate → 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester (211915-84-3)

Guidance literature:

With ammonium hydroxide; In dichloromethane; water; pH=8 - 10;

Reference yield: 95.0%

(4-cyanophenyl)glycine (42288-26-6) + ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate (212322-56-0) → 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester (211915-84-3)

Guidance literature:

(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;

With acetic acid; In Isopropyl acetate; for 2h; Reflux;

Reference yield: 82.0%

isopropyl 2?(4?cyanophenylamino)acetate + ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate (212322-56-0) → 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester (211915-84-3)

Guidance literature:

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

upstream raw materials:

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

4-methylamino-3-nitro-benzoic acid chloride

4-(methylamino)-3-nitrobenzoic acid

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

Downstream raw materials:

dabigatran etexilate

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

N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl] amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-β-alanine ethyl ester methanesulfonate

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

Refernces

• 1、 -. "Preparation method of anticoagulant drug dabigatran etexilate and analogues thereof". Paragraph 0039; 0041-0043. . Retrieved 2020/05/01.
• 2、 -. "Preparation method of dabigatran intermediate". . . Retrieved 2019/12/25.