429658-95-7

Basic information

• Product Name: Dabigatran ethyl AcOH Salt
• Synonyms: ethyl 3-(2-((4-carbamimidoylphenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate hydrochloride;Ethyl 3-(2-((4-carbaMiMidoylphenylaMino)Methyl)-1-Methyl-N-(pyridin-2-yl)-1H-ben;Ethyl 3-(2-((4-carbaMiMidoylphenylaMino)Methyl)-1-Methyl-N-(pyridin-2-yl)-1H-benzo[d]iMidazole-5-carboxaMido)propanoate;Dabigatran (ethyl ester);Alanine, N-[[2-[[[4-(aMinoiMinoMethyl)phenyl]aMino]Methyl]-1-Methyl-1H-benziMidazol-5-yl]carbonyl]-N-2-pyridinyl-, ethyl ester;Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-;DabigatranEtexilateMesylateinterMediates-6;ethyl 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate
• CAS NO: 429658-95-7
• Molecular Formula: C27H29N7O3
• Molecular Weight: 499.56426
• EINECS: -0
• Product Categories: Dabigatran impurity;benzimidazol
• Mol File: 429658-95-7.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 774.5 °C at 760 mmHg
• Flash Point: 422.2 °C
• Appearance: /
• Density: 1.31
• PKA: 12.92±0.50(Predicted)
• CAS DataBase Reference: Dabigatran ethyl AcOH Salt(CAS DataBase Reference)
• NIST Chemistry Reference: Dabigatran ethyl AcOH Salt(429658-95-7)
• EPA Substance Registry System: Dabigatran ethyl AcOH Salt(429658-95-7)

Safety Data

• Hazardous Substances Data: 429658-95-7(Hazardous Substances Data)

Usage

Uses

Dabigatran Ethyl Ester is an impurity of Dabigatran(D100090); an antithrombotic.

Upstream product

• 1307233-94-8 N-[[2-(chloromethyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridyl-β-alanine ethyl ester 
• 2498-50-2 4-aminobenzamidine dihydrochloride 
• 64-17-5 ethanol 
• 211915-84-3 3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester 
• 218168-58-2 ethyl 2-((4-cyanophenyl)amino)acetate 
• 948551-71-1 3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate 
• 1188417-09-5 1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide acetate salt 
• 429659-01-8 ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate 
• 82357-48-0 4-methylamino-3-nitro-benzoic acid chloride 
• 212322-56-0 ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate 
• 211915-06-9 dabigatran etexilate 
• 211915-06-9 dabigatran etexilate 

Downstream Products

• 1415506-19-2 3-[[[2-[[[4-[amino[[[(hexyloxy)carbonyl]amino]methyl]]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid 

Relevant articles and documents

Main degradation products of dabigatran etexilate evaluated by LC-UV and LC-ESI-MS, degradation kinetics and in vitro cytotoxicity studies

The present study reports the stability profile of an antithrombotic drug: dabigatran etexilate (DAB). The drug was subjected to thermal degradation at 60 °C and products formed were investigated by liquid chromatography-UV (LC-UV) and liquid chromatography-mass spectrometry (LC-ESI-MS). Chromatographic separation of the degradation products was performed on a GL Sciences Inc. Inertsil ODS-2 column (250 mm × 4.6 mm i.d., with a particle size of 5 μm and pore size of 110 ?) with mobile phase consisting of acetonitrile and ammonium acetate buffer (pH 5.5; 10 mmol L-1) (65:35, v/v) pumped at 1.0 mL min-1 flow rate. Column temperature was set at 30 °C and detection at 225 nm using a UV detector. LC-UV method previously validated was extended to LC-ESI-MS for the characterization of the degradation products (DP-01 and DP-02) formed, without complicated isolation or purification processes, based on retention times and confirmation of molecular weight. Degradation kinetics of DAB was also evaluated and could be described as a first-order process (R2 = 0.9900). Furthermore, no evidence of cytotoxicity in human mononuclear cells was observed for DAB degraded samples.

Preparation method of dabigatran etexilate intermediate

The invention relates to a preparation method of a dabigatran etexilate intermediate. The preparation method comprises the following steps: (1) carrying out addition on a compound III as shown in thefollowing formula and hydroxylamine to obtain a compound II under the catalysis of an alkali reagent; and (2) putting the compound II obtained in the step (1) into an organic solvent, and carrying outhydrogenation reduction reaction under the action of a catalyst to obtain a compound I shown in the following formula, namely the target product ethyl 3-(2-(((4-formamidinophenyl) amino) methyl)-1-methyl-N-(pyridine-2-yl)-1H-benzimidazole-5-formamide) propionate. The compound III is used as an initial reactant, and the compound II is obtained through addition reaction so that the use of a large amount of hydrogen chloride gas for preparing the imine ester hydrochloride is avoided; the compound I is prepared by hydrogenating and reducing the compound II, the reaction conditions are mild, and the safety of the preparation process is improved; meanwhile, the preparation method is simple in process step, the product is easy to purify, large-scale synthesis can be realized, and the industrialdevelopment prospect is relatively high.

Dabigatran etexilate mesylate preparation method

The invention belongs to the field of pharmaceutical synthesis, and provides a dabigatran etexilate mesylate preparation method, which comprises: carrying out a ring closure reaction on 3-[(3-amino-4-methylaminobenzoyl)(pyridine-2-yl)amino] ethyl propionate and chloroacetic anhydride to generate N-[[2-(chloromethyl)-1-methyl-1H-benzimidazole-5-yl]carbonyl]-N-2-pyridyl-beta-alanine ethyl ester, carrying out a condensation reaction on the N-[[2-(chloromethyl)-1-methyl-1H-benzimidazole-5-yl]carbonyl]-N-2-pyridyl-beta-alanine ethyl ester and 4-aminobenzamidine dihydrochloride to obtain 3-({2-[(4-amidino-phenylimino)-methylene]-1-methylene-1H-benzimidazole-5-carbonyl}-pyridine-2-imine)-ethyl propionate, carrying out ester forming on the 3-({2-[(4-amidino-phenylimino)-methylene]-1-methylene-1H-benzimidazole-5-carbonyl}-pyridine-2-imine)-ethyl propionate and hexyl chloroformate to obtain dabigatran etexilate, and carrying out salt forming on the dabigatran etexilate and methanesulfonic acid to obtain dabigatran etexilate mesylate. According to the present invention, the route of the method has characteristics of high yield, mild condition and convenient intermediate purification, and meets the requirements of industrial production.