To a solution of 5-(2,4-difluorophenyl)nicotinic acid (40.0 mg, 0.15 mmol) in DMF (0.7 mL) were added hydrochloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (49.3 mg, 0.18 mmol), EDC (33.9 mg, 0.18 mmol), HOBT (22.6 mg, 0.15 mmol) and triethylamine (0.10 mL, 0.74 mmol). The mixture was stirred at ambient temperature for 18 h. Purification by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title product, which was converted to hydrochloride salt using 2.0 M HCl in ether (47 mg). HRMS 424.1086. 1H NMR (400 MHz, CD3OD): δ 9.22 (s, 1H); 9.15 (s, 1H); 9.00 (s, 1H); 8.52 (s, 1H); 7.92 (d, J=8.4 Hz, 1H); 7.83-7.73 (m, 1H); 7.70 (d, J=8.4 Hz, 1H); 7.31-7.21 (m, 2H); 5.33-5.25 (m, 1H); 1.67 (d, J=7.1 Hz, 3H).
