Acetic Acid → HCID 178441965, compound

HRID 423187Notes

Reaction equation

HRID 423187 reaction equation
[CH:1]1([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4C=CO[N:19]=4)=[CH:14][CH:13]=3)[C:10](=[O:23])[C:9](O)=[C:8]2[C:25](=O)[C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:31]([OH:34])(=O)[CH3:32].O.[NH2:36][NH2:37]>O>[C:26]([C:25]1[C:8]2[CH:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:32]=[CH:31][O:34][N:19]=4)=[CH:14][CH:13]=3)[C:10](=[O:23])[C:9]=2[NH:36][N:37]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 25096959HCID 25096959, compound

Product 1

HCID 178441965HCID 178441965, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-cyclohexyl-4-(2,2-dimethylpropionoyl)-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-1,5-dihydropyrrol-2-one (0.10 g, 0.25 mmol) and acetic acid (1 mL) was added hydrazine monohydrate (0.036 mL, 0.75 mmol). The mixture was stirred at 85° C. for 3 hr. Water (80 mL) was added to the mixture, which was then extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (80 mL×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane). The crude product was recrystallized from ethyl acetate to give 3-tert-butyl-4-cyclohexyl-5-(4-isoxazol-3-ylphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.072 g, 71%) as colorless crystals.

Workup

  1. extractionwas then extracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate (80 mL×2)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)
  6. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3b59665357c8466e8c17fd7dba280357
Source dataset
uspto-grants-2012_01
Patent number
US08101644B2

Reaction notes

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