211915-84-3 | 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic Acid Ethyl Ester

Introduction
3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester is a white to off-white powder, anticoagulant drug; used in patients with non-valvular atrial fibrillation to reduce the risk of stroke and systemic embolism. The intermediate of the raw material drug dabigatran etexilate; the intermediate of dabigatran; is a kind of A new type of synthetic direct thrombin inhibitor, a prodrug of dabigatran, is a non-peptide thrombin inhibitor.

Specification of CAS: 211915-84-3 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester

Synthesis of CAS: 211915-84-3 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester

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

At 10-15 ° C, add the intermediate DGM1 (20g, 58mmol, 1.0eq), intermediate DGM2 (10.8g, 61mmol, 1.05eq) and 500mL dichloromethane to a 1000mL reaction flask, stir to dissolve, and then add EDCI ( 16.7g, 87mmol, 1.5eq), HOBt (11.7g, 87mmol, 1.5eq) and N, N-diisopropylethylamine (15g, 116mmol, 2eq),The temperature was raised to 30-35 ° C and the reaction was monitored by TLC. After the reaction,Add 200 mL of 10% acetic acid aqueous solution and 100 mL of dichloromethane, stir for 3 hours, let stand, and separate the organic phase. The organic phase is saturated aqueous sodium bicarbonate (200 mL × 1) and saturated aqueous sodium chloride (200 mL × 1) It was washed, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was concentrated under reduced pressure to obtain a crude solid. The crude product was recrystallized with 300 mL of ethanol to obtain 23.2 g of solid product DG1. Yield: 82%.

Reference:

Nantong Changyou Pharmaceutical Technology Co., Ltd.; Li Zebiao; Gu Wenchao; Zhang Qinghai; Ding Hongping; Lin Yanfeng CN110981858, 2020, A Location in patent: Paragraph 0039; 0041-0043

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