Hydrogen Peroxide → HCID 118080622, compound

HRID 1485802Notes

Reaction equation

HRID 1485802 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[C:7]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([C:22]3[CH:23]=[N:24][N:25]([CH:27]4[CH2:29][CH2:28]4)[CH:26]=3)=[C:17]([C:20]#[N:21])[CH:18]=2)[N:13]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:12][C@@H:11]1[CH3:36])(=[O:9])[CH3:8].OO>CS(C)=O>[C:7]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([C:22]3[CH:23]=[N:24][N:25]([CH:27]4[CH2:28][CH2:29]4)[CH:26]=3)=[C:17]([C:20](=[O:2])[NH2:21])[CH:18]=2)[N:13]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:12][C@@H:11]1[CH3:36])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 118080531HCID 118080531, compound

Product 1

HCID 118080622HCID 118080622, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium carbonate (0.002 g, 0.014 mmol) was added to a solution of isopropyl (S)-4-acetyl-6-cyano-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1 (2H)-carboxylate (0.010 g, 0.025 mmol) in dimethyl sulfoxide (2004), and the mixture was cooled in an ice bath. Hydrogen peroxide (30 wt %, 100 μL, 0.979 mmol) was added dropwise, the ice bath removed after 1 minute, and the reaction was allowed to warm to room temperature. Water was added, and the resulting precipitate was filtered and dried. The solid was purified by mass triggered preparatory HPLC. The product-containing fractions were combined and concentrated in a Genevac to afford isopropyl (S)-4-acetyl-6-carbamoyl-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate. MS (ESI, pos. ion) m/z 426 [M+H]+.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customthe ice bath removed after 1 minute
  3. additionWater was added
  4. filtrationthe resulting precipitate was filtered
  5. customdried
  6. customThe solid was purified by mass
  7. concentrationconcentrated in a Genevac

Sources & evidence

ORD record
ord-a4a5388bbe154a51a6652094d54ac00c
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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