Methanol → HCID 178522057, Verbindung

HRID 45845

Reaktionsgleichung

Reaktionsgleichung von HRID 45845
[F:1][C:2]1[C:7]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][NH:10][N:9]=2)=[C:6]([F:19])[CH:5]=[CH:4][C:3]=1[NH2:20].[F:21][C:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1N=C=O)([F:24])[F:23].CO.C[N:37](C)[CH:38]=[O:39]>>[F:1][C:2]1[C:7]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][NH:10][N:9]=2)=[C:6]([F:19])[CH:5]=[CH:4][C:3]=1[NH:20][C:38]([NH:37][C:28]1[CH:27]=[CH:26][C:25]([C:22]([F:21])([F:23])[F:24])=[CH:30][CH:29]=1)=[O:39]

Komponenten

5

Edukt 4

HCID 887MethanolHCID 6228DimethylformamideHCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 178507659HCID 178507659, Verbindung

Produkt 1

HCID 178522057HCID 178522057, Verbindung

Versuchsvorschrift

To 2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (70 mg, 0.25 mmol) (prepared as described in Example 22) in anhydrous N,N-dimethylformamide (2.5 mL) was added trifluoromethyl-phenylisocyanate (35 μL, 0.25 mmol) at 0° C. The reaction was allowed to warm to room temperature and it was stirred under nitrogen atmosphere for two days to yield a mixture of mono- and di-urea derivatives. Solvent was removed under reduced pressure. To the crude of reaction in methanol (3 mL) triethylamine (138 μL, 1 mmol) was added and the reaction was stirred at room temperature for two hours in order to transform the di-urea into the mono-urea derivative. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed successively with NaHCO3 saturated solution. The organic layer was dried over anhydrous sodium sulfate and filtered. The product was isolated by silica gel column chromatography eluting with methanol 10% in methylene chloride.

Aufarbeitung

  1. customto yield
  2. customSolvent was removed under reduced pressure
  3. additionwas added
  4. stirringthe reaction was stirred at room temperature for two hours in order
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed successively with NaHCO3 saturated solution
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe product was isolated by silica gel column chromatography
  11. washeluting with methanol 10% in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-5284df4d278648fda51d7a2d4b0516dc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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