Ethyl Acetate → HCID 22626658, compound

HRID 277935Notes

Reaction equation

HRID 277935 reaction equation
FC(F)(F)C([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30])=O.CC(=O)OCC>CO.[OH-].[Na+]>[NH2:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 9846345HCID 9846345, compound

Product 1

HCID 22626658HCID 22626658, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The 2-trifluoroacetamido-3-(2,4-difluorophenyl)-6-benzoyl-imidazo[1,2-a]pyridine (9.24 g, 20.8 mmol) was dissolved in 250 ml of MeOH and 170 ml of 1N NaOH. The solution was stirred at RT under N2 for 2 weeks. The precipitant was filtered and the filter cake was dissolved in 900 ml of EtOAc. The solution was washed with brine (3×50 ml), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was recrystalized from EtOAc/hexane to give 2 crops yielding 5.57 g. (76.8%). EA, MS(FD).

Workup

  1. filtrationThe precipitant was filtered
  2. dissolutionthe filter cake was dissolved in 900 ml of EtOAc
  3. washThe solution was washed with brine (3×50 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystalized from EtOAc/hexane
  8. customto give 2 crops
  9. customyielding 5.57 g

Sources & evidence

ORD record
ord-a79ec1d349e843048d34a2dae4d6eead
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

Loading…