To a solution of sodium chloride salt of 1-(5-fluoropyridin-2-yl)-3-(2-methyl-1,3-thiazol-5-yl)-1H-pyrazole-4-carboxylic acid (0.14 g, 0.25 mmol) in DMF (2.5 mL) was added (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (66.2 mg, 0.27 mmol), EDC (83.0 mg, 0.43 mmol), HOAT (16.9 mg, 0.12 mmol) and triethylamine (0.21 mL, 1.49 mmol). The mixture was stirred at 50° C. After 2 h, saturated aqueous NaHCO3 were added and the mixture was extracted with dichloromethane (3×). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane 85% dichloromethane/methanol) gave the title compound (72 mg). HRMS 493.1070 (M+1). 1H NMR (500 MHz, DMSO): δ 9.41 (s, 1H); 8.61 (s, 1H); 8.56 (s, 1H); 8.48 (s, 1H); 8.04-8.02 (m, 2H); 7.94 (d, J=8.4 Hz, 1H); 7.56 (d, J=8.3 Hz, 1H); 5.17-5.14 (m, 1H); 2.67 (s, 3H); 1.51 (d, J=7.1 Hz, 3H).
