1,2-Dichloroethane → N-(5-Methyl-4-isoxazolyl)-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

Participants

Reaction Steps

A mixture of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 100 mg, 0.30 mmol), EDC (115 mg, 0.60 mmol), and HOBT (92 mg, 0.60 mmol) in dimethylformamide (2 ml) was stirred in air at room temperature for 1 h, then 5-methyl-4-isoxazolamine (may be prepared as described in Description 93; 100 mg, 1.02 mmol) was added in one charge. The reaction mixture was stirred at 25° C. overnight. The solution was heated at 35° C. for 7 hours, then diluted with water (30 ml) and extracted with ethyl acetate (80 ml×3). The organic phase was washed with brine (60 ml×2), dried over anhydrous MgSO4, and concentrated. The residue was purified by chromatography (silica gel, 20 g, eluent: dichloromethane/methanol=60:1, 600 ml). The crude product was washed with methanol (2 ml×2), filtered, and dried in vacuum to yield the title compound. 23 mg.

Provenance & Evidence