N-hydroxy-4[[4-(4-trifluoromethylphenoxy)phenyl]sulfonyl]-1-(4-nitrophenylcarbonyl)-4-piperidinecarboxamide → N-hydroxy-4-[[4-(4-trifluoromethylphenoxy)phenyl]sulfonyl]-1-(4-aminophenylcarbonyl)-4-piperidinecarboxamide

HRID 353326Notes

Reaction equation

HRID 353326 reaction equation
[OH:1][NH:2][C:3]([C:5]1([S:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:10][CH2:9][N:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[O:12])[CH2:7][CH2:6]1)=[O:4].[H][H]>C(O)(=O)C.[Pd]>[OH:1][NH:2][C:3]([C:5]1([S:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:6][CH2:7][N:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[O:12])[CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 2

HCID 22707807N-hydroxy-4[[4-(4-trifluoromethylphenoxy)phenyl]sulfonyl]-1-(4-nitrophenylcarbonyl)-4-piperidinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 22707832N-hydroxy-4-[[4-(4-trifluoromethylphenoxy)phenyl]sulfonyl]-1-(4-aminophenylcarbonyl)-4-piperidinecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of N-hydroxy-4[[4-(4-trifluoromethylphenoxy)phenyl]sulfonyl]-1-(4-nitrophenylcarbonyl)-4-piperidinecarboxamide, the product of Example 113, (56.0 mg) dissolved in acetic acid (2.5 mL) was added to 4% palladium on carbon (20 mg) and placed under 43 psi hydrogen gas for 2.5 h. The reaction mixture was filtered through a pad of celite. The solvent was evaporated to afford N-hydroxy-4-[[4-(4-trifluoromethylphenoxy)phenyl]sulfonyl]-1-(4-aminophenylcarbonyl)-4-piperidinecarboxamide (50.2 mg) as a pale yellow solid. MS (ES) m/z 580 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3d5b8685150c4c6daa03ed3faf00ea8e
Source dataset
uspto-grants-2004_06
Patent number
US06750228B1

Reaction notes

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