4-Methylmorpholine → HCID 10206633, compound

Participants

Reaction Steps

Isobutyl chloroformate(0.161 g, 1.18 mmol) and N-methylmorpholine(0.150 g, 1.48 mmol) were added to an ice cold solution of 0.250 g (1.48 mmol) of 4-morpholino-2-butynoic acid in 10 mL of tetrahydrofuran under N2. After stirring for 30 min, a solution of 0.250 g (0.74 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 8 mL of pyridine was added and the mixture was stirred at 0° C. for 2 h. The reaction was quenched with ice water and then poured into saturated sodium bicarbonate and brine. The product was collected, washed with ethyl acetate, and dried in vacuo to give 0.096 g (27%) of yellow solid; ESMS m/z 490.1 (M+H+); mp 112-115° C.

Provenance & Evidence