HCID 169489376, compound → 4-[[(2S,4R)-1-(5-chloro-1-methylpyrazole-4-carbonyl)-2-methylpiperidin-4-yl]amino]-6,7-difluoro-1H-quinolin-2-one

Participants

Reaction Conditions

Reaction Steps

In a 25ml Biotage microwave vial, 4-chloro-6,7-difluoroquinolin-2(1H)-one (0.175 g, 0.81 mmol), ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone (0.208 g, 0.81 mmol) ,racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.051 g, 0.08 mmol), Cesium carbonate (0.793 g, 2.44 mmol), Palladium (II) acetate (0.018 g, 0.08 mmol) were taken were taken in toluene (10 mL) to give brown suspension. The reaction mass was subjected to microwave irradiation at 140 oC for 1 hour. The reaction ws monitored by LCMS, indicated required product formation. Workup: The reaction mixture was concentrated to dryness and purified by silica gel column chromatography using 0 to 20% Methanol in DCM and then purified by reverse phase chromatography to obtain 4-(((2S,4R)-1-(5-chloro-1-methyl-1H-pyrazole-4-carbonyl)-2-methylpiperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one (0.030 g, 8.48 %) as white solid. The compound was submitted for biological testing.

Provenance & Evidence