Hydrogen Peroxide → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 1641449Notes

Reaction equation

HRID 1641449 reaction equation
OO.C(OCC)(=O)C.[Br:9][C:10]1[CH2:14][CH:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[C:25](=[O:32])[NH:26][CH:27]([CH:29]2[CH2:31][CH2:30]2)[CH3:28])=[O:16])[N:12]([C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][N:34]=2)[N:11]=1>O>[Br:9][C:10]1[CH:14]=[C:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[C:25](=[O:32])[NH:26][CH:27]([CH:29]2[CH2:31][CH2:30]2)[CH3:28])=[O:16])[N:12]([C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][N:34]=2)[N:11]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 441856063-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Product 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamideYield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.13 g of a 30% hydrogen peroxide solution was added to an ethyl acetate 12 ml solution comprising 0.53 g of 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide, followed by reflux with heating. 30 hours later, the reaction liquid was stood to cool and poured to water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to obtain 0.32 g of the desired product.

Workup

  1. temperatureby reflux
  2. temperaturewith heating
  3. custom30 hours later, the reaction liquid
  4. temperatureto cool
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-576e9d3cf6644beeaa890b3285d9e027
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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