Water → N-[6-(Acetylamino)pyridin-3-yl]-4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2,2-trichloroethyl [6-(acetylamino)pyridin-3-yl]carbamate (277 mg, 0.848 mmol), 1-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine (200 mg, 0.771 mmol) and diisopropylethylamine (0.148 ml, 0.848 mmol) in dimethylsulfoxide (2.6 ml) was stirred at 70° C. for 18 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 161 mg (47.8%) of the desired product as a solid.

Provenance & Evidence