Potassium Carbonate → ethyl 3-(2-((4-(N-(hexyloxycarbonyl)carbamimidoyl)phenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate

Participants

Reaction Conditions

Reaction Steps

350 mL acetone, 250 mL water and 32.2 g potassium carbonate were stirred in round bottom flask at 25° C. The reaction mixture was cooled to 10° C. and 100 g of 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxy carbonylethyl)amide hydrochloride of Formula (E) was added. 15 mL acetone and 16.8 mL n-hexyl chloroformate were added to the reaction mixture and stirred for 1 hour. The precipitated product was filtered and washed with mixture of acetone and water. The wet-cake was dissolved in acetone and stirred for 30 min. The product was obtained by addition of water followed by filtration. The wet-cake thus obtained was washed with acetone and dried to obtain dabigatran etexilate of Formula (E). 50 g dabigatran etexilate and 500 mL ethyl acetate were stirred at 25° C. The reaction mixture was charcoalized and filtered. The filtrate was heated 75° C. to 80° C. and stirred for 30 minutes and cooled to 25° C. to 35° C. The reaction mixture was filtered and washed with ethyl acetate to obtain pure dabigatran etexilate of Formula (F).

Provenance & Evidence