3-(3-Benzyloxy-5-isopropoxy-benzoylamino)-pyrazole-1-carboxylic acid tert-butyl ester → tert-Butyl 3-[(3-hydroxy-5-propan-2-yloxy-benzoyl)amino]pyrazole-1-carboxylate

HRID 641157Notes

Reaction equation

HRID 641157 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]([CH:27]=[C:28]([O:30][CH:31]([CH3:33])[CH3:32])[CH:29]=2)[C:12]([NH:14][C:15]2[CH:19]=[CH:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:16]=2)=[O:13])C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:27]=[C:28]([O:30][CH:31]([CH3:33])[CH3:32])[CH:29]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:16]=1)=[O:13]

Participants

4

Reactant 1

HCID 574692013-(3-Benzyloxy-5-isopropoxy-benzoylamino)-pyrazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 57494686tert-Butyl 3-[(3-hydroxy-5-propan-2-yloxy-benzoyl)amino]pyrazole-1-carboxylateYield 107.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-[(3-phenylmethoxy-5-propan-2-yloxy-benzoyl)amino]pyrazole-1-carboxylate (76.4 g) in methanol (764 ml) was added 10% palladium on carbon (7.6 g) and the resulting mixture was stirred under an atmosphere of hydrogen at a pressure of 5 bar for 20 hours. The catalyst was removed by filtration through Celite. The filtrate was concentrated under vacuum to leave a solid (66 g). This was purified by flash chromatography on silica, eluting with ethyl acetate in isohexane (10 to 70%) to give the title compound (56.4 g).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-41ed54efb97b4f1aa42813e16135b078
Source dataset
uspto-grants-2010_04
Patent number
US07696191B2

Reaction notes

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