Hydrogen Peroxide → HCID 11637555, compound

HRID 1024398Notes

Reaction equation

HRID 1024398 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].C(=O)([O-])[O-:21].[K+].[K+].OO>CS(C)=O.O>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[CH:7][C:4]=1[C:5]([NH2:6])=[O:21]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 11499766HCID 11499766, compound

Product 1

HCID 11637555HCID 11637555, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The nitrile 30 (10 mg, 40 μmol) was dissolved in dimethyl sulfoxide (0.5 ml). To this was added potassium carbonate (20 mg) and 30% hydrogen peroxide in water (100 μl). The reaction was warmed to approximately 60 C for 15 minutes. The reaction was concentrated to dryness and triturated in water. The resulting precipitate was filtered and dried in-vacuo overnight to give 31 (10 mg, 93%). 1H NMR DMSO-d6 11.99 (s, 1H), 8.32 (d, 1H), 8.24 (m, 1H), 8.01 (m, 1H), 7.88 (d, 1H), 7.59 (s, 1H), 7.40 (s, 1H), 7.37 (m, 2H), 7.15 (dd, 1H), 4.00 (s, 3H). LC/MS (M+1)=268.

Workup

  1. temperatureThe reaction was warmed to approximately 60 C for 15 minutes
  2. concentrationThe reaction was concentrated to dryness
  3. customtriturated in water
  4. filtrationThe resulting precipitate was filtered
  5. customdried in-vacuo overnight

Sources & evidence

ORD record
ord-c322ddea131840018ec7c11c908b4a19
Source dataset
uspto-grants-2014_05
Patent number
US08722889B2

Reaction notes

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