{4-[4-(3-Methoxy-5-nitro-pyridin-2-yl)-phenyl]cyclohexyl}-acetic acid methyl ester → {4-[4-(5-Amino-3-methoxy-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester

HRID 76058Notes

Reaction equation

HRID 76058 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:22]([O:23][CH3:24])=[CH:21][C:20]([N+:25]([O-])=O)=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1>[Pd].CCOC(C)=O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:22]([O:23][CH3:24])=[CH:21][C:20]([NH2:25])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 66615844{4-[4-(3-Methoxy-5-nitro-pyridin-2-yl)-phenyl]cyclohexyl}-acetic acid methyl ester

Product 1

HCID 66615823{4-[4-(5-Amino-3-methoxy-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {4-[4-(3-Methoxy-5-nitro-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (0.14 g) in 10 Ml EtOAc was added 30 mg Pd/C. The reaction vessel was purged with hydrogen, then stirred overnight under a balloon atmosphere of hydrogen. Filtration through Celite followed by removal of solvent in vacuo afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.94-1.02 (m, 1H) 1.01 (s, 3H) 1.31 (td, J=12.57, 9.98 Hz, 2H) 1.64 (d, J=11.37 Hz, 4H) 2.09 (d, J=6.82 Hz, 2H) 3.44 (s, 3H) 3.59 (s, 3H) 5.25 (s, 2H) 6.52 (d, J=2.02 Hz, 1H) 7.02 (d, J=8.34 Hz, 2H) 7.47 (d, J=2.02 Hz, 1H) 7.54 (d, J=8.34 Hz, 2H); (M+H)+355.1.

Workup

  1. customThe reaction vessel was purged with hydrogen
  2. filtrationFiltration through Celite
  3. customfollowed by removal of solvent in vacuo

Sources & evidence

ORD record
ord-c4edf6af790344dabe16163efb837a08
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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