HCID 22181326, compound → HCID 22181423, compound

HRID 1796510Notes

Reaction equation

HRID 1796510 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]([CH3:27])[C:21](=[O:26])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH:17]=[CH:16][C:15]=2[N+:28]([O-])=O)=[O:12])=[CH:6][CH:5]=1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]([CH3:27])[C:21](=[O:26])[CH2:22][CH:23]([CH3:24])[CH3:25])[CH:17]=[CH:16][C:15]=2[NH2:28])=[O:12])=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 22181326HCID 22181326, compound

Product 1

HCID 22181423HCID 22181423, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Ethoxy-N-[5-[methyl(3-methyl-1-oxobutyl)amino]-2-nitrophenyl]-benzeneacetamide (1.05 g, 2.53 mmol) was dissolved in EtOAc (50 mL) containing a catalytic amount of 10% Pd/C. The solution was shaken under H2 atmosphere (35 psi) at rt overnight. The solution was filtered through celite and the solvent concentrated. LC/MS analysis showed that title compound was pure (>95%) and could directly be used for next step. Yield: 965 mg (99%). 1H NMR (400 MHz, CDCl3) δ 7.23 (d, J=8.8 Hz, 2H), 7.12 (s, 1H), 7.00 (s, 1H), 6.93 (d, J=8.8 Hz, 1H), 6.78 (m, 2H), 4.01 (q, J=7.0 Hz, 2H), 3.69 (s, 2H), 3.13 (s, 3H), 2.05 (m, 1H), 1.93 (d, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), 0.78 (d, J=6.8 Hz, 6H).

Workup

  1. filtrationThe solution was filtered through celite
  2. concentrationthe solvent concentrated

Sources & evidence

ORD record
ord-2f982fc0226c40f98b8e3cb9b06a1250
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

Loading…