Cyclohexene → HCID 18674103, compound

HRID 1635928Notes

Reaction equation

HRID 1635928 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:20]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CCCCC=1>[OH-].[Pd+2].[OH-].[C].C(O)C>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:20]=2[C:32]2[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=2)=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 18674187HCID 18674187, compound

Product 1

HCID 18674103HCID 18674103, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolvent

Procedure

Under a stream of argon gas, 0.11 g of 5-(4-benzyloxyphenylacetylamino)-3-(4-fluorophenyl)-1-methyl-4-(4-pyridyl)pyrazole, 22.9 mg of palladium hydroxide-carbon, and 8 ml of cyclohexene were added to 15 ml of ethanol followed by heating under reflux for 23 hours. After the reaction mixture was cooled to room temperature, the catalyst was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography using 30 g of silica gel [with an elution solvent comprising chloroform-methanol (100:0-40:1)]. Thus, 61.3 mg (69% yield) of the title compound was obtained as white crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 23 hours
  3. filtrationthe catalyst was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-1c98c1ff1e924f6887aade5ae011309a
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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