1,2-Dichloroethane → HCID 86657034, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2,4-difluorophenyl)-6-(2,2,2-trifluoro-1-hydroxyethyl)isonicotinic acid (0.15 g, 0.45 mmol) in DMF (2.5 mL) were added hydrochloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (0.16 g, 0.59 mmol), EDC (0.17 g, 0.90 mmol), HOAT (61.3 mg, 0.45 mmol) and triethylamine (0.38 mL, 2.7 mmol). The mixture was stirred at 60° C. After 1 h, the mixture was cooled to ambient temperature and saturated aqueous NaHCO3 was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The mixture was suspended in dichloromethane and the solid was filtered. The solid cake was washed with cold dichloromethane and dried under hi-vac. The product was treated with HCl (2.0 M in ether) to give the hydrochloride salt of the title compound (0.18 g). HRMS 522.1063 (M+1). 1H NMR (400 MHz, CD3OD): δ 8.48 (s, 1H); 8.17 (s, 1H); 8.09-7.99 (m, 2H); 7.89 (d, J=8.4 Hz, 1H); 7.65 (d, J=8.4 Hz, 1H); 7.10 (t, J=9.1 Hz, 2H); 5.28-5.18 (m, 2H); 1.62 (d, J=7.2 Hz, 3H).

Provenance & Evidence