HCID 178452255, compound → HCID 178452254, compound

HRID 1433140Notes

Reaction equation

HRID 1433140 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([C:19]3[CH:24]=[C:23]([Cl:25])[C:22]([O:26]CC4C=CC=CC=4)=[CH:21][C:20]=3[O:34]CC3C=CC=CC=3)=[N:16][NH:17][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]([C:19]3[CH:24]=[C:23]([Cl:25])[C:22]([OH:26])=[CH:21][C:20]=3[OH:34])=[N:16][NH:17][CH:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178452255HCID 178452255, compound

Product 1

HCID 178452254HCID 178452254, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (230 mg, 0.4 mmol) in ethyl acetate (15 ml) was hydrogenated over 10% palladium on carbon for 1.5 h. The suspension was filtered through celite, washing with dichloromethane:ethanol (1:1). The filtrate was concentrated to leave 4-[3-(5-chloro-2,4-dihydroxy-phenyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (Example 1) as a white solid (72 mg)

Workup

  1. filtrationThe suspension was filtered through celite
  2. washwashing with dichloromethane:ethanol (1:1)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-133c84882a1e4dd39b4780cf972a8759
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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