N-methyl-2-pyrrolidone → 7-Methoxy-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-4-phenylbenzo[d]thiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-7-methoxy-4-phenylbenzo[d]thiazole (100 mg, 363 μmol), 1-(6-methylpyrimidin-4-yl)piperidin-4-amine dihydrochloride (115 mg, 435 μmol) and Hunig's base (187 mg, 253 μL, 1.45 mmol) in dioxane (2 mL) was heated to 160° C. in a microwave oven for 30 minutes. N-Methyl-2-pyrrolidinone (0.5 mL) was added and the reaction was heated to 200° C. in a microwave oven for 2 hours. Water was added and the reaction was extracted twice with dichloromethane. The combined organic layers were washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel using a gradient from dichloromethane to dichloromethane/methanol 9:1 (v/v) as eluent to yield the title compound as a light brown solid (40 mg, 25%). MS ISP (m/e): 432.4 (100) [(M+H)+].

Provenance & Evidence