Sodium Hydroxide → HCID 136339024, compound

HRID 1437290Notes

Reaction equation

HRID 1437290 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:21]=[N:22][C:23](OC)=[CH:24][CH:25]=3)[N:18]=[C:17]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)=[O:29])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl.[CH2:38]([OH:40])C.[H][H].[OH-].[Na+]>C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[N:22][C:21]=3[O:40][CH3:38])[N:18]=[C:17]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)=[O:29])[CH:16]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 10050977HCID 10050977, compoundHCID 21887872Ethanol hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 136339024HCID 136339024, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-[5-(4-benzyloxyphenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carbonyl]-4-methylpiperazine (0.802 g) obtained in Example 18 in ethanol (15 mL), 10% palladium-carbon (0.466 g) and 1M HCl-ethanol (1.65 mL) were added, and the mixture was stirred at room temperature in a hydrogen atmosphere for 24 hours. After completion of the reaction, the atmosphere was changed to nitrogen, and the mixture was neutralized with aqueous sodium hydroxide. Insoluble matter was separated, and the residue was washed with methanol the filtrate was removed under reduced pressure, and the residue was partitioned between water and chloroform. Subsequently, the aqueous layer was extracted with chloroform. The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. After filtration, 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 a foamy substance (0.493 g, 69%).

Workup

  1. customAfter completion of the reaction
  2. customInsoluble matter was separated
  3. washthe residue was washed with methanol the filtrate
  4. customwas removed under reduced pressure
  5. customthe residue was partitioned between water and chloroform
  6. extractionSubsequently, the aqueous layer was extracted with chloroform
  7. washwashed with saturated brine
  8. dry with materialby drying over sodium sulfate anhydrate
  9. filtrationAfter filtration
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-9ec4f4174ecf42809f0c7e98f6cff8b8
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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