1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (163 mg, 0.65 mmol) was dissolved in 10 mL of dichloromethane and treated with EDCI (150 mg, 0.72 mmol), HOBt (88 mg, 0.65 mmol), N-methylmorpholine (0.2 mL, 1.5 mmol), and 4-(aminomethyl)-3-(trifluoromethyl)benzonitrile (130 mg, 0.65 mmol) at room temperature for 12 hours. The reaction mixture was concentrated and purified by preparative HPLC to provide N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamide (7 mg, 0.02 mmol, 2%) as a white solid. MS (ES+): m/e 434 [M+H]+.
