Water → N-[2-Chloro-4-({6-methoxy-7-[3-(4-pyridylthio)propoxy]-4-quinazolinyl}oxy)phenyl]-N'-propylurea

HRID 1375882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375882
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25])=[C:19]([Cl:30])[CH:18]=3)=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].[SH:39][C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1.O>CN(C)C=O>[Cl:30][C:19]1[CH:18]=[C:17]([O:16][C:10]2[C:9]3[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][S:39][C:40]4[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=4)=[C:7]([O:31][CH3:32])[CH:8]=3)[N:13]=[CH:12][N:11]=2)[CH:22]=[CH:21][C:20]=1[NH:23][C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22667067N-(4-{[7-(3-bromopropoxy)-6-methoxy-4-quinazolinyl]oxy}-2-chlorophenyl)-N'-propylureaHCID 178418431pyridine-4-thiol

Produkt 1

HCID 22667169N-[2-Chloro-4-({6-methoxy-7-[3-(4-pyridylthio)propoxy]-4-quinazolinyl}oxy)phenyl]-N'-propylureaAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A starting compound (N-(4-{[7-(3-bromopropoxy)-6-methoxy-4-quinazolinyl]oxy}-2-chlorophenyl)-N′-propylurea, 80 mg), potassium carbonate (138 mg), and 4-mercaptopyridine (22 mg) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was washed with ether to give 60 mg (yield 72%) of the title compound.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform-propanol (3/1)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was removed by distillation under the reduced pressure
  4. washThe residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-4c838b03a929480f9f5aee53e9578703
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169789B2

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