Morpholine → N-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide

To a mixture of 0.69 g (1.87 mmol) of 4-[(3-bromophenyl)amino]-7-methoxy-6-amino-3-quinolinecarbonitrile and 0.98 ml (5.6 mmol) of Hunig's base in 50 ml of dry THF at 0° C., with stirring, was added a THF solution containing 0.86 g (5 mmol) of 4-bromocrotonyl chloride dropwise. The mixture was stirred for a additional 0.5 hour and then was added to a solution of 4.89 ml (56 mmol) morpholine in 50 ml THF at 0° C. dropwise. The solution was stirred an additional 0.5 hour and then the mixture was poured into diluted sodium bicarbonate solution . The organic layer was separated and dried over sodium sulfate. The residue was chromatographed to give 0.38 g of grey solid: mass spectrum (electrospray, m/e): M+H 521.9 and 523.8.

1. stirringThe mixture was stirred for a additional 0.5 hour
2. stirringThe solution was stirred an additional 0.5 hour
3. customThe organic layer was separated
4. dry with materialdried over sodium sulfate
5. customThe residue was chromatographed

ORD 기록

ord-a686f6b8ed7b462a9a1fd56345527de9

출처 데이터셋

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06384051B1