Des-(N-2-pyridyl-β-alanine Ethyl Ester) Dabigatran Etexilate 5-Ethyl Carboxylate (Dabigatran IMpurity)

Base Information

• Chemical Name: Des-(N-2-pyridyl-β-alanine Ethyl Ester) Dabigatran Etexilate 5-Ethyl Carboxylate (Dabigatran IMpurity)
• CAS No.: 1408238-36-7
• Molecular Formula: C26H33N5O4
• Molecular Weight: 479.579
• Mol file: 1408238-36-7.mol

Synonyms:Des-(N-2-pyridyl-β-alanine Ethyl Ester) Dabigatran Etexilate 5-Ethyl Carboxylate (Dabigatran IMpurity);Dabigatran Etexilate Mesylate impurity H;ethyl (E)-2-(((4-(N'- ((hexyloxy)carbonyl)carbamimidoyl)p henyl)amino)methyl)-1-methyl-1Hbenzo[ d]imidazole-5-carboxylate

Chemical Property of Des-(N-2-pyridyl-β-alanine Ethyl Ester) Dabigatran Etexilate 5-Ethyl Carboxylate (Dabigatran IMpurity)

Chemical Property:

• PKA: 9.88±0.46(Predicted)
• PSA: 118.33000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 5.55760
• Storage Temp.: -20°C, Inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Des-(N-2-pyridyl-β-alanineEthylEster)DabigatranEtexilate5-EthylCarboxylate(DabigatranImpurity) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Des-(N-2-pyridyl-β-alanine ethyl ester) Dabigatran etexilate 5-ethyl carboxylate is a derivative of Dabigatran (D100090), an oral thrombin inhibitor used to prevent venous thromboembolism.

Technology Process of Des-(N-2-pyridyl-β-alanine Ethyl Ester) Dabigatran Etexilate 5-Ethyl Carboxylate (Dabigatran IMpurity)

There total 13 articles about Des-(N-2-pyridyl-β-alanine Ethyl Ester) Dabigatran Etexilate 5-Ethyl Carboxylate (Dabigatran IMpurity) 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: 87.0%

n-hexyl chloroformate (6092-54-2) + ethyl 2-{[(4-{carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-carboxylate (1408238-41-4) → ethyl 2-[[4-[(n-hexyloxycarbonyl)aminoiminomethyl]phenylamino]methyl]-1-methyl-1H-benzimidazole-5-carboxylate (1408238-36-7)

Guidance literature:

With sodium hydroxide; In water; acetone; at 10 - 25 ℃;

Reference yield: 74.3%

ethanol (64-17-5) + n-hexyl chloroformate (6092-54-2) + ethyl 3-(2-(((4-(ethoxy(imino)methyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionate → dabigatran etexilate (211915-06-9) + ethyl 2-[[4-[(n-hexyloxycarbonyl)aminoiminomethyl]phenylamino]methyl]-1-methyl-1H-benzimidazole-5-carboxylate (1408238-36-7)

Guidance literature:

ethanol; ethyl 3-(2-(((4-(ethoxy(imino)methyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propionate; With ammonium carbonate; at 0 - 25 ℃; for 12h; Inert atmosphere;

n-hexyl chloroformate; With potassium carbonate; In tetrahydrofuran; water; at 10 - 30 ℃; for 1h; Inert atmosphere;

Reference yield: 59.0%

n-hexyl chloroformate (6092-54-2) + ethyl 2-[[4-(aminoiminomethyl)phenylamino]methyl]-1-methyl-1H-benzimidazole-5-carboxylate hydrochloride (1422435-39-9) → ethyl 2-[[4-[(n-hexyloxycarbonyl)aminoiminomethyl]phenylamino]methyl]-1-methyl-1H-benzimidazole-5-carboxylate (1408238-36-7)

Guidance literature:

With triethylamine; In dichloromethane; for 2h; Reflux;

DOI:10.3987/COM-13-12746

upstream raw materials:

(4-cyanophenyl)glycine

4-Aminobenzonitrile

n-hexyl chloroformate

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

Refernces

• 1、 -. "Preparation method of high-purity dabigatran etexilate". Paragraph 0006; 0018; 0019. . Retrieved 2017/08/27.
• 2、 -. "DABIGATRAN ETEXILATE AND RELATED SUBSTANCES, PROCESSES AND COMPOSITIONS, AND USE OF THE SUBSTANCES AS REFERENCE STANDARDS AND MARKERS". . . Retrieved 2012/12/13.