Trifluoroacetic acid → HCID 72189976, compound

Participants

Reaction Steps

To a 0° C. solution of tert-butyl 4-{5-[2-(3-fluoroazetidin-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, 95 mg, 0.131 mmol) in dichloromethane (0.700 mL) 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-fluoroazetidin-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 (62 mg, 0.078 mmol) as a white fluffy solid. LCMS (M+H)+: 670.2. 1H NMR (500 MHz, CD3OD): δ 8.22 (m, 2H), 7.98 (s, 1H), 7.91 (d, 1H, J=8.7 Hz), 7.70 (s, 1H), 7.50 (m, 2H), 7.40 (m, 2H), 5.76 (d, 1H, J=8.7 Hz), 5.54 (br s, 0.5H), 5.43 (br s, 0.5H), 4.62 (d, 1H, J=17.1 Hz), 4.50 (m, 2H), 4.40 (m, 1H), 4.24 (m, 2H), 4.14 (d, 1H, J=17.0 Hz), 4.02 (s, 3H), 2.39 (s, 3H), 0.75 (d, 3H, J=6.5 Hz). RTA IC50: 12 nM.

Provenance & Evidence