4(3H)-Quinazolinone, 3-(2-chlorophenyl)-6-fluoro-2-methyl- → 3-(2-Chloro-phenyl)-6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one

HRID 897039

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH3:20].CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH:20]=[CH:23][N:24]([CH3:26])[CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

A mixture of 3-(2-chloro-phenyl)-6-fluoro-2-methyl-3,4-dihydro-quinazolin-4-one (1.0 g, 3.46 mmol) and dimethylformamide dimethyl acetal (0.92 mL, 6.92 mmol) in dimethylformamide (4 mL) was heated to 140° C. for 24 hours. The reaction was cooled to ambient temperature and concentrated at reduced pressure. The dark residue was triturated with methanol and the bright yellow crystalline solid which formed was collected and dried to give 1.075 g (90%) of 3-(2-chloro-phenyl)-6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one which had: mp 210-211° C.; 1H NMR δ 7.86 (d, J=12.3 Hz, 1 H), 7.79 (dd, J=3, 8.5 Hz, 1 H), 7.61-7.54 (m, 1 H), 7.51-7.29 (m, 5 H), 4.06 (d, J=12.3 Hz, 1 H), 2.80 (br s, 6 H). Analysis calculated for C18H15ClFN3O: C, 62.89; H, 4.40; N, 12.22. Found: C, 62.75; H, 4.28; N, 12.29.

Aufarbeitung

temperatureThe reaction was cooled to ambient temperature
concentrationconcentrated at reduced pressure
customThe dark residue was triturated with methanol
customthe bright yellow crystalline solid which formed
customwas collected
customdried

Quellen und Nachweise

ORD-Eintrag: ord-bc3b02814dc0452c87080d478d366964
Quelldatensatz: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06921764B2

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