2-Bromo-1-(4-fluorophenyl)ethan-1-one → 4-(2-{5-[2-(4-Fluoro-phenyl)-2-oxo-ethylamino]-2-methyl-phenyl amino}-oxazol-5-yl)-benzonitrile

HRID 244589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244589
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([NH:8][C:9]2[O:10][C:11]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:12][N:13]=2)[CH:7]=1.[F:23][C:24]1[CH:33]=[CH:32][C:27]([C:28](=[O:31])[CH2:29]Br)=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[F:23][C:24]1[CH:33]=[CH:32][C:27]([C:28](=[O:31])[CH2:29][NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([NH:8][C:9]3[O:10][C:11]([C:14]4[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=4)=[CH:12][N:13]=3)[CH:7]=2)=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 516892Sodium BicarbonateHCID 177573464-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile

Produkt 1

HCID 119656004-(2-{5-[2-(4-Fluoro-phenyl)-2-oxo-ethylamino]-2-methyl-phenyl amino}-oxazol-5-yl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile (60 mg, 0.207 mmol) in dimethylacetamide (3 mL) was added 4-fluorophenacyl bromide (45 mg, 0.207 mmol), NaHCO3 (18 mg, 0.207 mmol). The mixture was stirred at room temperature for 2 h. After removal of the solvent, the residue was treated with saturated aqueous NaHCO3 (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4 and concentrated. 4-(2-{5-[2-(4-Fluoro-phenyl)-2-oxo-ethylamino]-2-methyl-phenyl amino}-oxazol-5-yl)-benzonitrile was obtained after silica gel column chromatography (dichloromethane/ethanol: 9812) (38 mg, 43%) as beige solid.

Aufarbeitung

  1. customAfter removal of the solvent
  2. additionthe residue was treated with saturated aqueous NaHCO3 (10 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-41c7b4f081ea48a3bbfb18cd0ea93f90
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658659B2

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