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

HRID 398647Notes

Reaction equation

HRID 398647 reaction equation
[CH:1]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([CH:7]([CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:9])=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 99497883-cyclopentyl-2-(4-nitro-phenyl)-N-pyridin-2-yl-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 223152342-(4-amino-phenyl)-3-cyclopentyl-N-pyridin-2-yl-propionamideYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-cyclopentyl-2-(4-nitro-phenyl)-N-pyridin-2-yl-propionamide (130 mg, 0.38 mmol) in ethyl acetate (50 mL) and methanol (5 mL) was treated with a catalytic amount of 10% palladium on activated carbon (50 mg). The resulting mixture was shaken at 25° C. under 60 psi of hydrogen gas in a Parr apparatus for 24 h. At this time, the catalyst was removed by filtration through a plug of celite. The filtrate was concentrated in vacuo to afford 2-(4-amino-phenyl)-3-cyclopentyl-N-pyridin-2-yl-propionamide (99.9 mg, 84.3%) as a tan oil: EI-HRMS m/e calcd for C19H23N3O (M+) 309.1834, found 309.1849.

Workup

  1. customAt this time, the catalyst was removed by filtration through a plug of celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-53f53e59d79a456aa4e69d2af218ac53
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

Loading…