1,2-Dichloroethane → 8-(3,4-Difluorophenyl)-N-(4-methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Participants

Reaction Steps

To a solution of methyl 4-methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-ylcarbamimidothioate hydroiodide (1.85, 4.54 mmol) containing 5-chloro-2-(3,4-difluorophenyl)pentanoic acid (1.24, 5.00 mmol), EDC (0.87, 4.54 mmol) and 1-hydroxybenzotriazole hydrate (1.39 g, 9.08 mmol) in DMF (22.3 mL) was added DIPEA (1.98 mL, 11.4 mmol) and the reaction mixture was stirred at room temperature for 18 hours. Hydrazine monoydrate (0.57 mL, 18.2 mmol) was then added and the reaction mixture stirred at 70° C. for 5 h. The reaction mixture was then poured into water, extracted twice with ethyl acetate, and the combined organic layers washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica gel, 2×50 g, 0 to 20% methanol in dichloromethane) afforded the title compound (14 mg, 1%) as a light red foam.

Provenance & Evidence