Water → HCID 68420860, compound

HRID 1800374Notes

Reaction equation

HRID 1800374 reaction equation
FC(F)(F)C([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:33])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)[CH:18]=[CH:19][CH:20]=3)=[CH:10][N:9]2[CH:34]=1)=O.[OH-].[Na+].O>C(O)C>[NH2:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:33])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=4)[CH:18]=[CH:19][CH:20]=3)=[CH:10][N:9]2[CH:34]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86631979HCID 86631979, compound

Product 1

HCID 68420860HCID 68420860, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-({2-[(trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamide (400 mg, 0.787 mmol) produced in Example A1(vi) in ethanol (4.0 mL) was added 1N aqueous sodium hydroxide solution (8.0 mL), and the mixture was stirred at room temperature for 12 hr. Water (100 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→80/20), fractions containing the object product was concentrated under reduced pressure, and the residue was washed with ethyl acetate/diisopropyl ether (1:4) to give the title compound (350 mg, quantitative) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 mL)
  2. washThe organic layer was washed with saturated brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→80/20), fractions
  7. additioncontaining the object product
  8. concentrationwas concentrated under reduced pressure
  9. washthe residue was washed with ethyl acetate/diisopropyl ether (1:4)

Sources & evidence

ORD record
ord-630f8d7e9b6440aeaf74d81111f5c2bd
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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