HCID 90224876, compound → HCID 90224813, compound

HRID 1487095Notes

Reaction equation

HRID 1487095 reaction equation
[NH2:1][C:2]1([C:30]([NH2:32])=[O:31])[CH2:7][CH2:6][N:5]([S:8](/[CH:11]=[CH:12]/[C:13]2[C:18]([CH3:19])=[CH:17][C:16]([N:20]3[C:24]([CH3:26])([CH3:25])[C:23](=[O:27])[NH:22][C:21]3=[O:28])=[CH:15][C:14]=2[CH3:29])(=[O:10])=[O:9])[CH2:4][CH2:3]1>CO.CN(C)C=O.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1([C:30]([NH2:32])=[O:31])[CH2:7][CH2:6][N:5]([S:8]([CH2:11][CH2:12][C:13]2[C:14]([CH3:29])=[CH:15][C:16]([N:20]3[C:24]([CH3:26])([CH3:25])[C:23](=[O:27])[NH:22][C:21]3=[O:28])=[CH:17][C:18]=2[CH3:19])(=[O:9])=[O:10])[CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 90224876HCID 90224876, compound

Product 1

HCID 90224813HCID 90224813, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (E)-4-amino-1-((4-(5,5-dimethyl-2,4-dioxoimidazolidine-1-yl)-2,6-dimethylstyryl)sulfonyl)piperidine-4-carboxamide (1.3 g, 2.8 mmol) and palladium hydroxide on carbon (20% Pd) (wetted with approximately 50% water) (1.3 g) in methanol (21 mL) and dimethylformamide (7 mL) was stirred under hydrogen atmosphere at room temperature for four hours. The reaction mixture was filtered and washed, and then the filtrate was concentrated under reduced pressure to afford 4-amino-1-((4-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-2,6-dimethylphenethyl)sulfonyl)piperidin-4-carboxamide (998 mg, 77%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c076e89d0f7143db80bc8b9c3c30bdee
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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