N-(4-{[(4,4-Difluorocyclohexyl)methyl]amino}-3-nitrophenyl)acetamide → N-(3-Amino-4-{[(4,4-difluorocyclohexyl)methyl]amino}phenyl)acetamide

HRID 1987208Notes

Reaction equation

HRID 1987208 reaction equation
[F:1][C:2]1([F:23])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][C:11]=2[N+:20]([O-])=O)[CH2:4][CH2:3]1>CCOC(C)=O.[Pd]>[NH2:20][C:11]1[CH:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[CH:14]=[CH:15][C:10]=1[NH:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([F:23])([F:1])[CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 57441084N-(4-{[(4,4-Difluorocyclohexyl)methyl]amino}-3-nitrophenyl)acetamide

Product 1

HCID 57441085N-(3-Amino-4-{[(4,4-difluorocyclohexyl)methyl]amino}phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

N-(4-{[(4,4-Difluorocyclohexyl)methyl]amino}-3-nitrophenyl)acetamide (1.48 g, 4.52 mmol) was dissolved in 50 mL of EtOAc containing a catalytic amount of 10% Pd/C. The solution was shaken in a Parr hydrogenation apparatus under H2 atmosphere (45 psi) at rt for 24 h. The solution was filtered through Celite and the solvent was evaporated. Yield: 1.32 g (98%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.31-1.43 (m, 2 H), 1.64-1.73 (m, 2 H), 1.74-1.82 (m, 1 H), 1.89-1.93 (m, 1 H), 1.93-1.96 (m, 1 H), 2.08-2.17 (m, 5 H), 3.00 (d, J=6.64 Hz, 2 H), 3.27-3.46 (m, 2 H), 6.55 (d, J=8.40 Hz, 1 H), 6.70 (dd, J=8.40, 2.34 Hz, 1 H), 7.01 (s, 1 H), 7.13 (d, J=2.34 Hz, 1 H).

Workup

  1. filtrationThe solution was filtered through Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b5b72612cfe641388918c58058dd42e7
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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