Water → N-(2-Chloro-4-{[6-methoxy-7-(4-pyridylmethoxy)-4-quinazolinyl]oxy}phenyl)-N'-propylurea

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Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:37][C:38]4[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A starting compound (N-{2-chloro-4-[(7-hydroxy-6-methoxy-4-quinazolinyl)oxy]phenyl}-N′-propylurea, 80 mg), potassium carbonate (138 mg), and 4-chloromethylpyridine hydrochloride (41 mg), were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at 80° C. for 3 hr. Water was added to the reaction mixture, followed by extraction with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC to give 65 mg (yield 66%) of the title compound.

Aufarbeitung

extractionfollowed by extraction with chloroform-propanol (3/1)
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was removed by distillation under the reduced pressure
customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag: ord-8509164283b24589bc5dc7d70692dfab
Quelldatensatz: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07169789B2

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