Acetyl chloride → N-Acetyl-N-{2-chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-propylurea

HRID 1375863

Reaktionsgleichung

Reaktionsgleichung von HRID 1375863
[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][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25].[H-].[Na+].[C:32](Cl)(=[O:34])[CH3:33]>O1CCCC1>[C:32]([N:23]([C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:7][C:2]=1[Cl:1])[C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25])(=[O:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 9549295Krn-633

Produkt 1

HCID 69353433N-Acetyl-N-{2-chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-propylureaAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-phenyl}-N′-propylurea 100 mg) was dissolved in anhydrous tetrahydrofuran (30 ml), and sodium hydride (60 wt %, 88 mg) was added to the solution. The mixture was stirred at room temperature for 15 min. Next, acetyl chloride (63 μl) was added to the reaction solution, and the mixture was stirred at room temperature for additional 2 hr. The solvent was removed by distillation under the reduced pressure, and water was added to the residue. The mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC by development with chloroform/acetone to give 27 mg (yield 26%) of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for additional 2 hr
  2. customThe solvent was removed by distillation under the reduced pressure, and water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by HPLC by development with chloroform/acetone

Quellen und Nachweise

ORD-Eintrag
ord-9271b39b3c8c4e4ea6291735aeac74d7
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169789B2

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