Triethylamine → N-(5-Acetyl-4-methyl-1,3-thiazol-2-yl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}urea

HRID 1348844

Reaktionsgleichung

Reaktionsgleichung von HRID 1348844
[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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[C:43]([C:46]1[S:50][C:49]([NH2:51])=[N:48][C:47]=1[CH3:52])(=[O:45])[CH3:44]>C(Cl)(Cl)Cl.O>[C:43]([C:46]1[S:50][C:49]([NH:51][C:35]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][C:18]=2[F:23])=[O:41])=[N:48][C:47]=1[CH3:52])(=[O:45])[CH3:44]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 7208825-Acetyl-2-amino-4-methylthiazoleHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Produkt 1

HCID 22637136N-(5-Acetyl-4-methyl-1,3-thiazol-2-yl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}ureaAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (30 mg) was dissolved in chloroform (3 ml) to prepare a solution. Triethylamine (0.3 ml) and a solution of triphosgene (27 mg) in chloroform (0.2 ml) were then added thereto, and the mixture was stirred at room temperature for 30 min. Next, a solution of 5-acetyl-2-amino-4-methylthiazole (64 mg) in chloroform (0.6 ml) was added thereto, and the mixture was further stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The extract was washed with saturated brine and was dried over anhydrous sodium sulfate. The organic layer was concentrated under the reduced pressure, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give 6 mg of the title compound.

Aufarbeitung

  1. customto prepare a solution
  2. stirringthe mixture was further stirred at room temperature overnight
  3. extractionthe mixture was subjected to separatory extraction with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated under the reduced pressure
  7. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ecd254eb004640c7924b87438c3e1fb6
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211587B2

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