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

HRID 1987225Notes

Reaction equation

HRID 1987225 reaction equation
[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])=[CH:12][C:11]=2[N+:22]([O-])=O)[CH2:4][CH2:3]1>CCOC(C)=O.CO.[Pd]>[NH2:22][C:11]1[CH:12]=[C:13]([NH:16][S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])[CH:14]=[CH:15][C:10]=1[NH:9][CH2:8][CH:5]1[CH2:4][CH2:3][C:2]([F:1])([F:25])[CH2:7][CH2:6]1

Participants

5

Reactant 1

HCID 11516373N-(4-(((4,4-Difluorocyclohexyl)methyl)amino)-3-nitrophenyl)ethanesulfonamide

Product 1

HCID 11559310N-(3-amino-4-{[(4,4-difluorocyclohexyl)methyl]amino}phenyl)ethanesulfonamideYield 103.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-{[(4,4-Difluorocyclohexyl)methyl]amino}-3-nitrophenyl)ethanesulfonamide (23.4 g) and Pd/C 10% in EtOAc (800 mL) were shaken together overnight under H2 atmosphere (50 PSI) in a Parr hydrogenation apparatus. The reaction mixture was diluted with MeOH (400 mL) and filtered over celite bed. The solvent was removed to provide the desired title product (22.2 g) as beige solid.

Workup

  1. filtrationfiltered over celite bed
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-87ad012c63f94080a6dfb9d4c3527591
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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