Triphosgene → N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamide

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Reaction Steps

Bis(trichloromethyl)carbonate (60.6 mg, 0.20 mmol) was added portion-wise to 4-(2-amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride (Example 3, 129 mg, 0.51 mmol) and TEA (0.285 mL, 2.04 mmol) in DCM (2 mL) under 1 minute at rt. After stirring for 20 min, a solution of 1-(6-methylpyridin-2-yl)piperazine (CAS 55745-89-6, 90 mg, 0.51 mmol) and TEA (0.142 mL, 1.02 mmol) in DCM (2 mL) was added drop-wise and the reaction was stirred for 90 min. The volatiles were removed before the reaction mixture was diluted with MeOH, filtered and purified by preparative HPLC. Fractions were pooled and freeze-dried to give N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamide (76 mg, 36%).

Provenance & Evidence