Diisopropylamine → HCID 89096175, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-(Azetidin-3-ylamino)-1-(2-ethoxy-ethyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile hydrochloride salt (1 eq, 0.050 g, 0.16 mmole) in dichloromethane at −10° C. was added acryloyl chloride (1.1 eq, 0.005 g, 0.055 mmole) followed by the addition of diisopropylamine (1.5 eq, 0.031 g, 0.075 mmole, 0.05mL). 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-(1-Acryloyl-azetidin-3-ylamino)-1-(2-ethoxy-ethyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile as a yellow solid (0.008 g, 28% calc M+H 367, obs M+H 367).

Provenance & Evidence