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

HRID 2296955Notes

Reaction equation

HRID 2296955 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 solution 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 10% palladium on activated carbon (50 mg). The reaction mixture was shaken under 60 psi of hydrogen gas at 25° C. for 18 h. The catalyst was then removed by filtration through a pad of celite and washed with ethyl acetate. 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 C21H23N3O (M+) 309.1841, found 309.1849.

Workup

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

Sources & evidence

ORD record
ord-0114056b2c82492e8995562d88063a34
Source dataset
uspto-grants-2002_12
Patent number
US06489485B2

Reaction notes

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