Methanesulfonic Acid → N-[3-(1H-Imidazol-2-ylamino)-4-methyl-phenyl]-3-trifluoromethyl-benzamide

Participants

Reaction Steps

A mixture of N-(2,2-diethoxyethyl)carbodiimide (398 mg, 2.51 mmol), 3-amino-4-methyl-phenyl]-3-trifluoromethyl-benzamide (649 mg, 2.20 mmol), methanesulfonic acid (143 μL, 2.20 mmol) in ethanol (25 mL) is heated at reflux for 16 hours. An additional portion of N-(2,2-diethoxyethyl)carbodiimide (525 mg, 3.32 mmol) and methanesulfonic acid (143 μL, 2.20 mmol) are added. After an additional 3 hours refluxing, the reaction mixture is concentrated. The residue is dissolved in HCl (6N, 5 mL) and ethanol (5 mL). After stirring overnight, the reaction mixture is concentrated and basified with 25% NaOH solution to a pH of 14. The mixture is stirred for 30 minutes, extracted with CH2Cl2, dried, concentrated and purified by column chromatography (silica gel, eluting with 7N NH3 in methanol:dichloromethane from 2% to 4%) to give the title compound.

Provenance & Evidence