Dabigatran iMpurity O

Base Information

• Chemical Name: Dabigatran iMpurity O
• CAS No.: 948551-71-1
• Molecular Formula: C27H28N6O4
• Molecular Weight: 500.557
• Mol file: 948551-71-1.mol

Synonyms:Dabigatran iMpurity O;3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate

Chemical Property of Dabigatran iMpurity O

Chemical Property:

• PSA: 136.45000
• LogP: 3.86458

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Ethyl3-(3-(2-((4-Cyanophenyl)amino)acetamido)-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 3-(3-(2-((4-Cyanophenyl)amino)acetamido)-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate is an impurity of both Dabigatran (D100090) and Dabigatran Etexilate (D100150).

Technology Process of Dabigatran iMpurity O

There total 8 articles about Dabigatran iMpurity O 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: 99.3%

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

Guidance literature:

(4-cyanophenyl)glycine; With 1,1'-carbonyldiimidazole; In dichloromethane; at 0 - 5 ℃; for 6h; Large scale;

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;

Reference yield:

4-(2-imidazol-1-yl-2-oxoethylamino)benzonitrile + ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate (212322-56-0) → 3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate (948551-71-1)

Guidance literature:

In toluene; at 50 ℃; for 3h;

Reference yield:

ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate (429659-01-8) → 3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate (948551-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 65 percent / H₂ / 10percent Pd/C / methanol / 20 °C

2.1: CDI / tetrahydrofuran / 50 °C

2.2: tetrahydrofuran / 24 h / Heating

With hydrogen; 1,1'-carbonyldiimidazole; 10percent Pd/C; In tetrahydrofuran; methanol;

DOI:10.1021/jm0109513

upstream raw materials:

(4-cyanophenyl)glycine

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

4-methylamino-3-nitro-benzoic acid chloride

4-(methylamino)-3-nitrobenzoic acid

Downstream raw materials:

dabigatran etexilate

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

3-[[[2-[[[4-[amino[[[(hexyloxy)carbonyl]amino]methyl]]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid

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

Refernces

• 1、 -. "Industrial preparation method of dabigatran". Paragraph 0039; 0040; 0041; 0042. . Retrieved 2017/08/28.
• 2、 -. "PROCESSES FOR THE PREPARATION OF DABIGATRAN ETEXILATE AND INTERMEDIATES THEREOF". . . Retrieved 2016/03/14.