Ethyl Acetate → HCID 68891436, compound

HRID 902207Notes

Reaction equation

HRID 902207 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH:7]2[CH2:12][CH2:11][C:10]3([C:20]4[C:15](=[CH:16][CH:17]=[N:18][CH:19]=4)[C:14](=[O:21])[O:13]3)[CH2:9][CH2:8]2)[NH:4][N:3]=1.[CH2:22](Cl)[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[N:3]([CH2:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[N:4]=[C:5]([CH:7]2[CH2:12][CH2:11][C:10]3([C:20]4[C:15](=[CH:16][CH:17]=[N:18][CH:19]=4)[C:14](=[O:21])[O:13]3)[CH2:9][CH2:8]2)[CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 107572-ChloroacetophenoneHCID 11430Potassium CarbonateHCID 68893646HCID 68893646, compound

Product 1

HCID 68891436HCID 68891436, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-Amino-5-[3-oxospiro[6-azaisobenzofuran-1(3H),1-cyclohexan]-4′-yl]-1H-pyrazole (180 mg, 0.633 mmol), phenacyl chloride (150 mg, 0.94 mmol) and potassium carbonate (180 mg, 1.27 mmol) were stirred overnight at room temperature in N,N-dimethylformamide (10 mL). The mixture was stirred for further 1 hour at 80° C. The reaction solution was cooled down to room temperature and ethyl acetate was added thereto. The reaction solution was washed with water and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to remove the solvent. The residue was separated and purified by a silica gel column chromatography (C-300, methanol:chloroform=1:50 to 1:30) to obtain the title compound (26.5 mg, 10.4%) as a cis and trans mixture.

Workup

  1. temperatureThe reaction solution was cooled down to room temperature
  2. washThe reaction solution was washed with water and saturated brine
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto remove the solvent
  6. customThe residue was separated
  7. custompurified by a silica gel column chromatography (C-300, methanol:chloroform=1:50 to 1:30)

Sources & evidence

ORD record
ord-b157539ee26d4b3ab6b9bcda8f52cc8f
Source dataset
uspto-grants-2008_04
Patent number
US07365079B2

Reaction notes

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