Triethylamine → N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamide

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Reaction Steps

1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (100 mg, 0.4 mmol) was dissolved in 3 mL of dichloromethane and treated with EDCI (115 mg, 0.6 mmol), HOBt (65 mg, 0.48 mmol), triethylamine (0.44 mL, 3.2 mmol), and 1-{4-bromo-2-[(trifluoromethyl)oxy]phenyl}methanamine (152 mg, 0.4 mmol) at 8° C. for 4 days. 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 (3.5 mg, 0.02 mmol, 2%) as a white solid. MS (ES+): m/e 503, 505 [M+H]+. 1H NMR (400 MHz, methanol-D4) 7.4 (m, 2H), 7.2 (d, 1H), 4.8 (2H under MeOH peak), 4.3 (s, 2H), 3.1 (m, 2H), 2.9 (s, 3H), 2.5 (m, 1H), 2.3 (s, 3H), 1.8 (m, 2H), 1.6 (m, 2H)

Provenance & Evidence