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

HRID 1874534Notes

Reaction equation

HRID 1874534 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 68419251N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(trifluoromethyl)benzamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-(3-aminophenoxy)pyridin-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, the precipitated product was collected by filtration and dried with air to give the title compound (3.95 g, 83%) as a colorless powder.

Workup

  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 precipitated product was collected by filtration
  10. customdried with air

Sources & evidence

ORD record
ord-461a155f154e42e7a3e731f605b12ec1
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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