Nitrogen → N-[4-[(3-Bromophenyl)amino]-3-cyano-6-quinolinyl]-4-diethylamino-2-butynamide

Isobutyl chloroformate (0.261 g, 1.91 mmol) was dropwise added into an ice cold solution of 4-diethylamino-2-butynoic acid (0.456 g, 2.94 mmol) and N-methylmorpholine (0.294 g, 2.94 mmol) in 50 mL of tetrahydrofuan under N2. After stirring for 30 min, a solution of 0.5 g (1.47 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 3 mL of pyridine was added dropwise and the mixture was stirred at 0° C. for 2 hr. The reaction was quenched with ice water, poured into saturated sodium bicarbonate and brine, and extracted with ethyl acetate. The ethyl acetate layer was concentrated and purified by thin-layer chromatography eluted with 15% methanol in ethyl acetate. The product was collected, and dried in vacuo to give 0.2 g (28.5%) of pale greenish yellow solid; ESMS m/z 476.2, 478.2 (M+H+); mp 133-135° C.

1. stirringthe mixture was stirred at 0° C. for 2 hr
2. customThe reaction was quenched with ice water
3. additionpoured into saturated sodium bicarbonate and brine
4. extractionextracted with ethyl acetate
5. concentrationThe ethyl acetate layer was concentrated
6. custompurified by thin-layer chromatography
7. washeluted with 15% methanol in ethyl acetate
8. customThe product was collected
9. customdried in vacuo

ORD record

ord-6e482544bde54f41b2cbbe59ea3acdf9

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06002008