Hydrogen Peroxide → HCID 86700757, compound

HRID 2272549Notes

Reaction equation

HRID 2272549 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:18]2[C:13](=[C:14]([N:19]3[CH:23]=[C:22]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[N:21]=[CH:20]3)[CH:15]=[CH:16][CH:17]=2)[C:12]([C:30]([F:33])([F:32])[F:31])=[N:11]1)[C:5]#[N:6].[OH-:34].[Na+].OO.[Cl-].[NH4+]>CS(C)=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:18]2[C:13](=[C:14]([N:19]3[CH:23]=[C:22]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[N:21]=[CH:20]3)[CH:15]=[CH:16][CH:17]=2)[C:12]([C:30]([F:33])([F:32])[F:31])=[N:11]1)[C:5]([NH2:6])=[O:34]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 86700758HCID 86700758, compound

Product 1

HCID 86700757HCID 86700757, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound (20a) (50 mg) in DMSO (0.5 mL) were added 4N aqueous sodium hydroxide solution (56 μL) and aqueous hydrogen peroxide solution (25 μL), and the mixture was stirred at room temperature for 10 minutes. After completion of the reaction, an aqueous ammonium chloride solution was added to the reaction solution, and then the mixture was partitioned with ethyl acetate. The organic layer was washed with saturated brine and dried by the addition of anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was subjected to slurry washing with acetonitrile. The precipitated solid was collected by filtration and dried to obtain compound (24) (33 mg, yield 63%) as a milky white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was partitioned with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried by the addition of anhydrous sodium sulfate
  5. customAfter removal of the solvent
  6. customby evaporation
  7. washto slurry washing with acetonitrile
  8. filtrationThe precipitated solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-f9d5fcdbbb66418995146a3ded5faaa0
Source dataset
uspto-grants-2015_09
Patent number
US09120780B2

Reaction notes

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