Water → ethyl 4-(5-chloropyrazin-2-yl)-2-[(3R,4S)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-bromo-4-(5-chloropyrazin-2-yl)-1,3-thiazole-5-carboxylate (Intermediate 47, 120 mg, 0.3960 mM) was added to a solution of 3,4-dichloro-N-[(3R,4S)-3-methoxypiperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (WO2006087543, 127 mg, 0.4158 mM) and N,N-diisopropylethylamine (159.6 mg, 1.247 mM) in N-methyl 2-pyrrolidinone (1.0 mL) and the resulting reaction mixture was stirred at 50-55° C. for 1 h. The reaction mixture was cooled to room temperature and then poured into water (40 mL). The resulting solid was collected by filtration and dried to afford ethyl 4-(5-chloropyrazin-2-yl)-2-[(3R,4S)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylate 140 mg (90%) of as an off-white solid.

Provenance & Evidence