Triethylamine → 3-Acetylamino-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-5-(trifluoromethyl)-benzamide

Participants

Reaction Conditions

Reaction Steps

Diethylcyanophosphonate (Aldrich, Buchs, Switzerland; 0.66 mL, 4.0 mmol) is added to a stirred mixture of 4-methyl-N-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine (554 mg, 2.0 mmol), 3-acetylamino-5-(trifluoromethyl)-benzoic acid (495 mg, 2.0 mmol) and triethylamine (1.12 mL, 8.0 mmol) in 10 mL N,N-dimethylformamide at 20° C. under an argon atmosphere. After stirring for 18 hours at 20° C., the mixture is treated with saturated aqueous solution of sodium hydrogen carbonate and extracted twice with ethyl acetate. The combined extracts are dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to afford a crude product. The crude product is purified by column chromatography on silica gel, eluent dichloromethane/methanol/aqueous ammonia. The pure fractions are combined, the solvent is evaporated off under reduced pressure and the residue is crystallised from ethyl acetate-hexane to give the title compound as a cream crystalline solid.

Provenance & Evidence