Hydrogen Peroxide → HCID 54755246, compound

HRID 868972Notes

Reaction equation

HRID 868972 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH2:13][CH2:14][C:15]1[N:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-:24].[K+].[K+].OO>CS(C)=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]=[C:3]1[CH2:13][CH2:14][C:15]1[N:20]=[C:19]([C:21]([NH2:22])=[O:24])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 70117041HCID 70117041, compound

Product 1

HCID 54755246HCID 54755246, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)-picolinonitrile (10 mg, 0.035 mmol) in dimethyl sulfoxide (2 mL) at 0° C. was added potassium carbonate (24 mg, 0.175 mmol) and hydrogen peroxide (12 mg, 0.350 mmol). After stirring at room temperature for 1 h, the mixture was quenched with sat. NaHSO4 (aq.), and extracted with EtOAc (30 mL×2). The organic phase was dried and concentrated under reduced pressure. The residue was purified by prep-HPLC to give a white solid (3 mg). MS (ESI): m/z 307 [M+H]+.

Workup

  1. customthe mixture was quenched with sat. NaHSO4 (aq.)
  2. extractionextracted with EtOAc (30 mL×2)
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-9643350b94334b9a9479579bb0859d2f
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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