Hydroxyamine hydrochloride → 3-[2-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

HRID 229693Notes

Reaction equation

HRID 229693 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:27])[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].Cl.[NH2:29]O.[C:31]([O-:34])(=O)[CH3:32].[Na+]>C(O)C.O>[CH3:32][C:31]1[O:34][N:29]=[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[C:10](=[O:27])[N:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:14]=2)[N:2]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 517045Sodium Acetate2×HCID 9924495Perampanel

Product 1

HCID 101582413-[2-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-oneYield 6.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

53 mg of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 10 ml of ethanol containing 20% of water. 19 mg of hydroxylamine hydrochloride and 17 mg of sodium acetate were added thereto, followed by heating under reflux for 24 hours. Further, 19 mg of hydroxylamine hydrochloride and 17 mg of sodium acetate were added thereto, followed by heating under reflux for 36 hours. After cooling to room temperature, the mixture was evaporated, and the resulting crystals were washed with water, dried, and 50 mg of amidoxime compound was collected by filtration. 20 mg of the product was dissolved in 4 ml of toluene. 16 mg of acetic anhydride was added thereto, followed by heating under reflux for 96 hours. After cooling to room temperature, the mixture was neutralized with potassium carbonate under ice-cooling. After extracting with ethyl acetate, the extract was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 4 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 24 hours
  3. temperatureby heating
  4. temperatureunder reflux for 36 hours
  5. customthe mixture was evaporated
  6. washthe resulting crystals were washed with water
  7. customdried
  8. filtration50 mg of amidoxime compound was collected by filtration
  9. dissolution20 mg of the product was dissolved in 4 ml of toluene
  10. addition16 mg of acetic anhydride was added
  11. temperatureby heating
  12. temperatureunder reflux for 96 hours
  13. temperatureAfter cooling to room temperature
  14. temperaturecooling
  15. extractionAfter extracting with ethyl acetate
  16. washthe extract was successively washed with water and brine
  17. dry with materialdried over anhydrous magnesium sulfate
  18. customThe solvent was evaporated
  19. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-65889a384e1f41d58b4459565c11ee44
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

Loading…