Triphosgene → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}-N'-(2-propynyl)urea

HRID 1375846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375846
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.Cl.[CH2:37]([NH2:40])[C:38]#[CH:39].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:28]([NH:40][CH2:37][C:38]#[CH:39])=[O:34])=[C:18]([F:23])[CH:17]=1

Komponenten

7

Edukt 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 11205720Prop-2-ynylamine hydrochlorideHCID 218902744-((6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline

Produkt 1

HCID 22667153N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}-N'-(2-propynyl)ureaAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene (47 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, propargylamine hydrochloride (29 mg) was added to the reaction solution, and the mixture was further stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and 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 washed with chloroform to give 21 mg (yield 33%) of the title compound.

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. washThe residue was washed with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-6681d1f6c3d442959e6d4878d9769245
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169789B2

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