Diisopropylamine → HCID 89052513, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-(4-Fluoro-benzyl)-2-oxo-4-piperazin-1-yl-1,2-dihydro-quinoline-3-carbonitrile hydrochloride salt (1 eq, 0.150 g, 0.41 mmole) in dichloromethane at −10° C. was added acryloyl chloride (1.1 eq, 0.054 g, 0.45 mmole) followed by the addition of diisopropylamine (1.5 eq, 0.083 g, 0.62 mmole, 0.103 mL). The resulting solution stirred at 10° C. for 1 hour then warmed to RT and stirred for an additional 2 hours. The reaction was quenched into ice cooled water and extracted with ethyl acetate (25 mL×3). Combined organic phase was washed consecutively with water, brine before drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 4-(4-Acryloyl-piperazin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile as a yellow solid (0.043 g, 25% calc M+H 417, obs M+H 417).

Provenance & Evidence