Pyridine → HCID 23118602, Verbindung

HRID 1348831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1348831
[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.N1C=CC=CC=1.ClC(Cl)(O[C:34](=[O:40])OC(Cl)(Cl)Cl)Cl.Cl.[NH2:43][C:44]1[S:45][C:46]([CH3:50])=[C:47]([CH3:49])[N:48]=1>C(Cl)(Cl)Cl.O>[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]([NH:20][C:34]([NH:43][C:44]2[S:45][C:46]([CH3:50])=[C:47]([CH3:49])[N:48]=2)=[O:40])=[C:18]([F:23])[CH:17]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 94429TriphosgeneHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)

Produkt 1

HCID 23118602HCID 23118602, VerbindungAusbeute 40,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (95 mg) was dissolved in chloroform (3 ml) and pyridine (0.2 ml) to prepare a solution. A solution of triphosgene (45 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, 2-amino-4,5-dimethylthiazole hydrochloride (54 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Iced water was added to the reaction solution, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine and was then dried over anhydrous sodium sulfate. The dried organic layer was filtered and was then concentrated. Ether was added to the residue for crystallization, and the crystal was collected by filtration. The crystal was purified by chromatography (chloroform:acetone=2:1) to give 29 mg of the title compound.

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. filtrationThe dried organic layer was filtered
  6. concentrationwas then concentrated
  7. additionEther was added to the residue for crystallization
  8. filtrationthe crystal was collected by filtration
  9. customThe crystal was purified by chromatography (chloroform:acetone=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-6c800eccd9224e279120d3f77d3542ed
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211587B2

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