Pyridine → HCID 178452465, compound

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 2-(4-(5-amino-1H-pyrazol-3-yl)phenyl)morpholine-4-carboxylate (100 mg, 0.29 mmol) was dissolved in a mixture of tetrahydrofurane/dichloromethane 2:3 (1.5 ml) then pyridine (46 mg, 0.047 ml, 0.58 mmol) and 4-dimethylaminopyridine (1.7 mg, 0.014 mmol) were added at 0° C. After 5 min, 4-fluorobenzoyl chloride (55.2 mg, 0.348 mmol) was addded and the reaction mixture was stirred at 0° C. for 1 h. The cooling bath was removed and the reaction mixture was allowed to stir at room temperature overnight. The reaction was quenched by addition of 1M citric acid (3 ml) and was extracted with ethyl acetate (5 ml). The organic layer was dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (silica gel, hepatne/ethyl acetate 1:1). Isolation of an off-white solid (100 mg, 74%), MS (ISP): 411.2 (100%, [M-tBu+H]+), 467.2 (66%, [M+H]+).

Provenance & Evidence