Potassium Chloride → 3-(5-Chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide

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Reaction Steps

To a solution of 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)benzoic acid (20 mg, 0.07 mmol) in DMF (0.7 mL) were added the potassium chloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (33.6 mg, 0.09 mmol), HATU (0.05 M in DMA; 0.21 mL, 0.10 mmol) and diisopropylamine (60 μL, 0.34 mmol). The mixture was stirred at ambient temperature. After 30 min, the mixture was filtered and the filtrate was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (25 mg). FIRMS 480.1302 (M+1). 1H NMR (400 MHz, CDCl3): δ 8.58 (s, 1H); 8.36 (s, 1H); 8.20 (d, J=4.9 Hz, 2H); 8.04 (s, 1H); 7.78-7.61 (m, 3H); 7.42-7.30 (m, 2H); 5.33-5.23 (m, 1H); 1.69 (s, 6H), 1.63 (d, J=7.1 Hz, 3H).

Provenance & Evidence