6-[3-Cyclopentyl-2-(4-nitro-phenyl)-propionylamino]-nicotinic acid methyl ester → 6-[2-(4-Amino-phenyl)-3-cyclopentyl-propionylamino]-nicotinic acid methyl ester

HRID 2296958Notes

Reaction equation

HRID 2296958 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:28])[CH:12]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:6][CH:5]=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:28])[CH:12]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)[CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)=[N:6][CH:5]=1

Participants

6

Reactant 2

HCID 233945786-[3-Cyclopentyl-2-(4-nitro-phenyl)-propionylamino]-nicotinic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 207070986-[2-(4-Amino-phenyl)-3-cyclopentyl-propionylamino]-nicotinic acid methyl esterYield 100.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-[3-cyclopentyl-2-(4-nitro-phenyl)-propionylamino]-nicotinic acid methyl ester (300 mg, 0.75 mmol) in ethyl acetate (30 mL) and methanol (5 mL) was treated with 10% palladium on activated carbon (30 mg). The reaction mixture was shaken under 60 psi of hydrogen gas at 25° C. for 16 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 6-[2-(4-amino-phenyl)-3-cyclopentyl-propionylamino]-nicotinic acid methyl ester (277.4 mg, quant) as a pale yellow glass: mp 65-68° C.; EI-HRMS m/e calcd for C21H25N3O3 (M+) 367.1893, found 367.1899.

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-3c060196d626441f923992ec83fe4b16
Source dataset
uspto-grants-2002_12
Patent number
US06489485B2

Reaction notes

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