1,1'-Carbonyldiimidazole → HCID 72189374, compound

Participants

Reaction Steps

A solution of 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzohydrazide (Step A, 108 mg, 0.147 mmol) in THF (1.5 mL) was treated with N,N-carbonyldiimidazole (71.6 mg, 0.442 mmol). The reaction was stirred at room temperature overnight. The reaction was purified directly by silica gel chromatography, eluting with a gradient of 25-100% ethyl acetate/hexanes to give the titled compound. LCMS (M+H)+: 760.5. 1H NMR (CDCl3, 500 MHz): δ 9.08 (br, 1H), 8.22 (d, 1H), 8.18 (s, 1H), 7.89 (s, 1H), 7.78 (s, 1H), 7.74 (s, s, 3H), 7.49 (d, 1H), 7.36 (d, 1H), 5.68 (d, 1H), 5.51 (m, 0.5H), 5.40 (m, 0.5H), 4.73 (d, 1H), 4.47 (m, 3H), 4.31 (m, 2H), 4.01 (m, s, 4H), 2.38 (s, 3H), 0.76 (d, 3H). RTA IC50: 12 nM.

Provenance & Evidence