4-[(Cyclohexylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide → 3-Amino-4-[(cyclohexylmethyl)amino]-N,N-bis(2,2,2-trifluoroethyl)benzamide

HRID 1296175Notes

Reaction equation

HRID 1296175 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:27]=[CH:26][C:12]([C:13]([N:15]([CH2:21][C:22]([F:25])([F:24])[F:23])[CH2:16][C:17]([F:20])([F:19])[F:18])=[O:14])=[CH:11][C:10]=2[N+:28]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[NH2:28][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][C:9]=1[NH:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:13]([N:15]([CH2:21][C:22]([F:23])([F:24])[F:25])[CH2:16][C:17]([F:19])([F:20])[F:18])=[O:14]

Participants

4

Reactant 1

HCID 589117434-[(Cyclohexylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 586645193-Amino-4-[(cyclohexylmethyl)amino]-N,N-bis(2,2,2-trifluoroethyl)benzamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

4-[(Cyclohexylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (110 mg, 0.249 mmol) was dissolved in 15 mL of EtOAc containing a catalytic amount of 10% Pd/C. The solution was shaken in a Parr hydrogenation apparatus under H2 atmosphere (40 psi) overnight at rt. The solution was filtered through Celite and the solvent concentrated. The title product was used directly for the next step without further purification. Yield: 102 mg (99%). MS (ESI) (M+H)+ 411.9.

Workup

  1. filtrationThe solution was filtered through Celite
  2. concentrationthe solvent concentrated
  3. customThe title product was used directly for the next step without further purification

Sources & evidence

ORD record
ord-d702cb5094fd47739198ff2ade9833b8
Source dataset
uspto-grants-2007_07
Patent number
US07244850B2

Reaction notes

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