Diisopropylethylamine → 3-amino-N-(5-chloro-2-methylbenzyl)isoxazole-5-carboxamide

Participants

Reaction Steps

To a solution of 3-aminoisoxazole-5-carboxylic acid (492 mg, 3.84 mmol) in DMF (16 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.87 g, 4.22 mmol) at 0° C. The resulting solution was stirred for 5 min, after which time, 1-(5-chloro-2-methylphenyl)methanamine (598 mg, 3.84 mmol) and N,N-diisopropylethylamine (2.0 mL, 12 mmol) was added. The solution was stirred at room temperature for 0.5 h. The reaction solution was diluted with ethyl acetate and water, the organic layer was separated and dried over Na2SO4, filtered and concentrated. The residue was recrystallized with ethyl acetate and hexanes to give product (730 mg, 71%). LCMS calculated for C12H13ClN3O2(M+H)+: m/z=266.1.

Provenance & Evidence