2-Methoxyethanol → HCID 10088698, 화합물

반응식

[CH:1]1([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13](F)=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][C:8]=2[C:20]#[N:21])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:24][O:25][CH2:26][CH2:27][OH:28]>>[CH:1]1([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:28][CH2:27][CH2:26][O:25][CH3:24])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][C:8]=2[C:20]#[N:21])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

반응물 3

HCID 80192-Methoxyethanol

HCID 24758Sodium hydride

HCID 234980904-Cyclopentylamino-7-fluoro-6-methoxy-3-quinolinecarbonitrile

생성물 1

HCID 10088698HCID 10088698, 화합물

실험 절차

A mixture of 4-cyclopentylamino-7-fluoro-6-methoxy-3-quinolinecarbonitrile (150 mg, 0.53 mmol) and sodium hydride (53 mg, 2.21 mmol) in 1.6 mL of 2-methoxyethanol is heated at reflux for 30 minutes, then cooled to room temperature. The reaction mixture is partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparative thin layer chromatography, eluting with 5% methanol in dichloromethane, followed by trituration with methanol and diethyl ether, provides 95 mg of 4-cyclopentylamino-6-methoxy-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 87-90° C.