2-Methoxyethanol → HCID 10088698, Verbindung
Reaktionsgleichung
[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]1Komponenten
4
Versuchsvorschrift
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.