Cesium carbonate → HCID 118208529, compound

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (320 mg, 0.99 mmol) and 5-(1-iodoethyl)-1,3-oxazolidin-2-one (160 mg, 0.66 mmol) were added to a solution of N-[4-(difluoromethyl)pyridin-2-yl]-4-methyl-6-(1H-pyrazol-4-yl)pyridin-2-amine (100 mg, 0.33 mmol) in DMF (1 mL) under a nitrogen atmosphere at 20° C. The mixture was stirred under nitrogen and heated to 80° C. for 12 hours. The reaction mixture was cooled to 20° C. and then diluted with brine (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by prep-TLC (ethyl acetate) to afford racemic 5-[4-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methylpyridin-2-yl)-1H-pyrazol-1-yl]-5-ethyl-1,3-oxazolidin-2-one. MS ESI calc'd. for C20H21F2N6O2 [M+H]+ 415. found 415. Racemic 5-[4-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methylpyridin-2-yl)-1H-pyrazol-1-yl]-5-ethyl-1,3-oxazolidin-2-one was separated by SFC (Chiralpak AD, 3 um particle size; 60% [ethanol with 0.05% diethylamine] in CO2) to afford:

Provenance & Evidence