Hydrogen Peroxide → HCID 19432819, compound

HRID 1736545Notes

Reaction equation

HRID 1736545 reaction equation
[OH-:1].[K+].OO.[C:5]([N:9]1[C:13]([NH2:14])=[C:12]([C:15]#[N:16])[C:11]([CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:10]1)([CH3:8])([CH3:7])[CH3:6]>O.C(O)C>[C:5]([N:9]1[C:13]([NH2:14])=[C:12]([C:15]([NH2:16])=[O:1])[C:11]([CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[N:10]1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 14797Potassium HydroxideHCID 19432810HCID 19432810, compound

Product 1

HCID 19432819HCID 19432819, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To potassium hydroxide (4.95 g, 0.09 mol) in 50% water/ethanol (83 ml) was added 30% hydrogen peroxide (6.7 ml, 0.06 mol) followed by 1-tert-butyl-3-(cyclohexylmethyl)-5-amino-1H-pyrazole-4-carbonitrile (2.8 g, 0.01 mol). The reaction mixture was stirred at room temperature for 24 hours, then was heated on a steam bath for 4 hours. More 30% hydrogen peroxide was added (6.5 ml, 0.057 mol) and the reaction mixture was heated for an additional 2 hours. The solvent was removed in vacuo, water was added and the residue was extracted with ethyl acetate (2×). The organic layer was washed with brine, dried over anhydrous MgSO4 and the solvent was removed in vacuo. The residue was purified by preparative thin layer chromatography on silica eluting with ethyl acetate (100%) to afford 0.34 g (11%) of 1-tert-butyl-3-(cyclohexylmethyl)-5-amino-1H-pyrazole-4-carboxamide as an amber oil.

Workup

  1. temperaturewas heated on a steam bath for 4 hours
  2. temperaturethe reaction mixture was heated for an additional 2 hours
  3. customThe solvent was removed in vacuo, water
  4. additionwas added
  5. extractionthe residue was extracted with ethyl acetate (2×)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified by preparative thin layer chromatography on silica eluting with ethyl acetate (100%)

Sources & evidence

ORD record
ord-405a2aa6a78f4bdfb3f584a3ec3c99e9
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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