Diisopropylethylamine → 2-(2,4-Difluorophenyl)-6-(2-methylpyrimidin-5-yl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}isonicotinamide

Participants

Reaction Steps

To a solution of 2-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)isonicotinic acid (21.3 mg, 0.05 mmol) in DMF (0.5 mL) were added hydrochloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (27.0 mg, 0.07 mmol), HATU (0.5 M in DMF; 0.16 mL, 0.08 mmol) and diisopropylethylamine (65 μL, 0.37 mmol). The mixture was stirred at ambient temperature. After 25 min, the mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound, which was converted to hydrochloride salt using 2.0 M HCl in ether (31 mg). HRMS 516.1453 (M+1). 1H NMR (400 MHz, CDCl3): δ 9.34 (s, 2H), 8.42 (s, 1H), 8.24-8.15 (m, 1H), 8.09 (s, 1H), 8.06 (s, 1H), 7.68 (d, J=8.3 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.11-7.04 (m, 1H), 6.97 (t, J=9.8 Hz, 1H), 6.85 (d, J=7.0 Hz, 1H), 5.37-5.30 (m, 1H), 2.83 (s, 3H), 1.69 (d, J=7.1 Hz, 3H).

Provenance & Evidence