Water → 4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(pyridin-4-yl)piperazine-1-carboxamide

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Reaction Steps

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (271 mg, 0.610 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.129 ml, 0.610 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 80° C. for 3 hours. Water was poured to the reaction mixture, and the resulting solution 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 (methanol ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 98.3 mg (44.1%) of the desired product as a solid.

Provenance & Evidence