Sodium Hydroxide → HCID 10068169, compound

HRID 1437287Notes

Reaction equation

HRID 1437287 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25](CC4C=CC=CC=4)[CH:24]([CH3:35])[CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1.[H][H].[OH-].[Na+]>C(O)C.Cl.C(O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH:24]([CH3:35])[CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 10254026HCID 10254026, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10068169HCID 10068169, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 21887872Ethanol hydrochlorideSolvent

Procedure

To a solution of 1-[1-(6-methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]-4-benzyl-3-methylpiperazine (0.459 g) obtained in Example 14 in ethanol (10 mL), 1M HCl-ethanol (0.980 mL) and 10% palladium-carbon (123 mg) were added at room temperature. The resultant mixture was stirred in a hydrogen atmosphere for 5.5 hours. After the atmosphere was changed to nitrogen, the mixture was neutralized to pH 8 with 1M aqueous sodium hydroxide, followed by removal of insoluble matter through filtration. Solvent of the filtrate was removed under reduced pressure, and then the residue was partitioned between water and chloroform. The aqueous layer was extracted with chloroform. The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. The resultant mixture was subjected to filtration, and the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as an oily product (0.250 g, 67%).

Workup

  1. customfollowed by removal of insoluble matter through filtration
  2. customSolvent of the filtrate was removed under reduced pressure
  3. customthe residue was partitioned between water and chloroform
  4. extractionThe aqueous layer was extracted with chloroform
  5. washwashed with saturated brine
  6. dry with materialby drying over sodium sulfate anhydrate
  7. filtrationThe resultant mixture was subjected to filtration
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-de9730b0eb864421aa3601e93cdfa52c
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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