Isopropanol → 4-[3-Benzamido-4-fluoroanilino]-4,7,8-trimethoxyquinazoline hydrochloride

HRID 1357703

Reaktionsgleichung

Reaktionsgleichung von HRID 1357703
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[Cl:19][C:20]1[C:29]2[C:24](=[C:25]([O:34][CH3:35])[C:26]([O:32][CH3:33])=[C:27](OC)[CH:28]=2)[N:23]=[CH:22][N:21]=1.[CH:36]([OH:39])(C)C>>[ClH:19].[C:10]([NH:9][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[F:1])[NH:8][C:20]1([O:39][CH3:36])[C:29]2[C:24](=[C:25]([O:34][CH3:35])[C:26]([O:32][CH3:33])=[CH:27][CH:28]=2)[N:23]=[CH:22][NH:21]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

4

Edukt 3

HCID 3776IsopropanolHCID 11148928N-(5-Amino-2-fluorophenyl)benzamideHCID 227323114-Chloro-6,7,8-trimethoxyquinazoline hydrochloride

Produkt 1

HCID 1784873324-[3-Benzamido-4-fluoroanilino]-4,7,8-trimethoxyquinazoline hydrochlorideAusbeute 53 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-(2-Fluoro-5-aminophenyl)benzamide (276 mg) was added to a suspension of 4-chloro-6,7,8-trimethoxyquinazoline hydrochloride (293 mg) in isopropanol (8 ml) and the resultant mixture stirred and heated to 80° C. for 18 hours. The mixture was cooled to ambient temperature and the precipitated solid was isolated, washed with isopropanol then diethyl ether to yield the title compound as a solid (257 mg, 53%); NMR: 4.0 (s, 3H), 4.01 (s, 3H), 4.07 (s, 3H), 7.42 (t, 1H), 7.52 (m, 2H), 7.62 (m, 2H), 8.0 (m, 3H), 8.35 (s, 1H), 8.72 (s, 1H), 10.28 (s, 1H), 11.84 (broad s, 1H); m/s: M+H+ 449.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe precipitated solid was isolated
  3. washwashed with isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-d58bce8cd4c14de0a169f40a8de9ab5b
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593333B1

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