Trifluoroacetic acid → HCID 72189977, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-{5-[2-(3,3-difluoroazetidin-1-yl)-4-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (Step A, 98 mg, 0.132 mmol) in dichloromethane (0.700 mL), cooled to 0° C. was added TFA (0.700 mL). The ice bath was removed and the reaction mixture was stirred for 1 hour. Upon completion the solvent was removed under reduced pressure and the resultant residue was dissolved in acetonitrile:water (1:1) for direct purification by reverse phase HPLC (C18) followed by lyophilization of appropriate fractions to yield 4-{5-[2-(3,3-difluoroazetidin-1-yl)-4-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoic acid (50.4 mg, 0.063 mmol) as a white fluffy solid. LCMS (M+H)+: 688.1. 1H NMR (500 MHz, CD3OD) δ8.27 (s, 1H), 8.23 (s, 1H), 7.97 (s, 1H), 7.91 (d, 1H, J=7.8 Hz), 7.71 (s, 1H), 7.50 (m, 2H), 7.39 (m, 2H), 5.76 (d, 1H, J=8.6 Hz), 4.67 (d, 1H, J=17.0 Hz), 4.53 (m, 4H), 4.38 (m, 1H), 4.16 (d, 1H, J=17.0 Hz), 4.01 (s, 3H), 2.39 (s, 3H), 0.75 (d, 3H, J=6.5 Hz). RTA IC50: 9 nM.

Provenance & Evidence