Imidazole → HCID 118021435, compound

Participants

Reaction Steps

Methyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfonyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (INTERMEDIATE 46, 125 mg, 0.169 mmol), 1,4-dioxane (1.1 mL) and imidazole (57.6 mg, 0.846 mmol) were stirred at 80° C. for 20 minutes in a 1 dram vial. LCMS shows about 2/3 conversion to target. Dropped temperature to 40° C., and stirred overnight, at which time LCMS showed reaction is complete. The reaction was directly purified by silica gel chromatography, eluting with 20-100% ethyl acetate/hexanes to give the titled compound. 1H NMR (CDCl3, 500 MHz): δ 8.64 (s, 1H), 8.56 (s, 1H), 8.30 (d, 1H), 8.00 (s, 1H), 7.94 (d, 1H), 7.90 (s, 2H), 7.75 (s, 2H), 7.57 (d, 1H), 7.33 (d, 1H), 7.22 (s, 1H), 5.75 (d, 1H), 4.91 (d, 1H), 4.46 (m, 1H), 4.20 (d, 1H), 4.03 (s, 3H), 3.94 (s, 3H), 2.39 (s, 3H), 0.81 (d, 3H).

Provenance & Evidence