Hydrogen Peroxide → HCID 58243929, compound

HRID 389120Notes

Reaction equation

HRID 389120 reaction equation
[OH-:1].[Na+].OO.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C@H:13]([C:15]2[N:16]([CH3:32])[C:17]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[C:28]([F:31])([F:30])[F:29])=[N:18][N:19]=2)[CH3:14])=[N:10][CH:11]=1.O>C(O)C>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C@H:13]([C:15]2[N:16]([CH3:32])[C:17]([C:20]3[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:1])=[CH:22][C:21]=3[C:28]([F:31])([F:29])[F:30])=[N:18][N:19]=2)[CH3:14])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 58244103HCID 58244103, compound

Product 1

HCID 58243929HCID 58243929, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1M aqueous sodium hydroxide solution (0.73 ml) and a 30% hydrogen peroxide solution (0.1 ml) were added to a solution of 4-(5-{(1S)-1-[(5-bromopyridin-2-yl)oxy]ethyl}-4-methyl-4H-1,2,4-triazol-3-yl)-3-(trifluoromethyl)benzonitrile (50 mg) in ethanol (3 ml) in an ice bath, followed by stirring at room temperature for 3 hours, and a 1M aqueous sodium hydroxide solution (0.42 ml) was added thereto, followed by stirring overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate twice. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Ethyl acetate (1 ml) was added to the residue and the precipitated solid was washed with ethyl acetate and then diethylether to obtain, as a white solid 4-(5-{(1S)-1-[(5-bromopyridin-2-yl)oxy]ethyl}-4-methyl-4H-1,2,4-triazol-3-yl)-3-(trifluoromethyl)benzamide (29.2 mg).

Workup

  1. stirringby stirring overnight
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionEthyl acetate (1 ml) was added to the residue
  7. washthe precipitated solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-f4ec7dbf799849dc97f604ea8adab05a
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

Loading…