3-(Trifluoromethyl)benzoyl chloride → N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide

HRID 1800371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800371
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>CN(C)C(=O)C>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([O:7][C:6]2[CH:5]=[C:4]([NH:3][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 684192875-(3-Aminophenoxy)pyridin-2-amine dihydrochloride

Produkt 1

HCID 68419251N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(trifluoromethyl)benzamideAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(3-aminophenoxy)pyridine-2-amine dihydrochloride (3.5 g, 12.7 mmol) in N,N-dimethylacetamide (30 mL) was added 3-(trifluoromethyl)benzoylchloride (2.80 g, 13.4 mmol), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, 5% aqueous sodium hydrogen carbonate solution (100 mL) was added to the residue, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with water (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate (30 mL)/hexane (20 mL) was added to the obtained residue, and the obtained precipitate was collected by filtration and air-dried to give the title compound (3.95 g, 83%) as a colorless powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 5% aqueous sodium hydrogen carbonate solution (100 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (200 mL)
  4. washThe organic layer was washed with water (100 mL) and saturated brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionEthyl acetate (30 mL)/hexane (20 mL) was added to the obtained residue
  9. filtrationthe obtained precipitate was collected by filtration
  10. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-1f847b9c022b404aafc3fcf3e8bc9875
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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