3-Cyclopentyl-2-(4-nitro-phenyl)-N-thiazol-2-yl-propionamide → 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

HRID 2296938Notes

Reaction equation

HRID 2296938 reaction equation
[CH:1]1([CH2:6][CH:7]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([CH:7]([CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 223151063-Cyclopentyl-2-(4-nitro-phenyl)-N-thiazol-2-yl-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 99488022-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamideYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-cyclopentyl-2-(4-nitro-phenyl)-N-thiazol-2-yl-propionamide (345 mg, 1.0 mmol) in ethyl acetate (100 mL) was treated with 10% palladium on activated carbon (34.5 mg). The reaction mixture was stirred under 60 psi hydrogen gas at 25° C. for 6 h. The catalyst was then removed by filtration through a pad of celite and was washed with ethyl acetate. The filtrate was concentrated in vacuo to give 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (288.3 mg, 91.4%) as a yellow solid: mp 102-107° C.; EI-HRMS m/e calcd for C17H21N3OS (M+) 315.1405, found 315.1401.

Workup

  1. customThe catalyst was then removed by filtration through a pad of celite
  2. washwas washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e1c9053af38c4494a2a815164403e497
Source dataset
uspto-grants-2002_12
Patent number
US06489485B2

Reaction notes

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