Ethanol → HCID 11373433, compound

HRID 2354173Notes

Reaction equation

HRID 2354173 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:32])=[C:11]([NH:13][C:14](=[O:31])[C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][C:16]=3[N+:28]([O-])=O)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[CH2:33](O)C>[Pd]>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[CH:9][C:10]([CH3:32])=[C:11]([N:13]3[C:14](=[O:31])[C:15]4[C:16](=[CH:17][C:18]([N:21]5[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]5)=[CH:19][CH:20]=4)[N:28]=[CH:33]3)[CH:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 702EthanolHCID 66918770HCID 66918770, compound

Product 1

HCID 11373433HCID 11373433, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-(4-methylpiperazin-1-yl)-2-nitrobenzamide (0.23 g) and 10% palladium on carbon (0.04 g) in ethanol (30 ml) was agitated under a hydrogen atmosphere for 16 hours. The reaction mixture was filtered through diatomaceous earth (Celite®) and the filtrate evaporated to dryness to give the title compound as a glass (0.16 g); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.68 (m, 2H), 2.22 (s, 3H), 2.24 (s, 3H), 2.43 (m, 4H), 2.85 (m, 1H), 3.19 (m, 4H), 6.18 (s, 1H), 6.25 (m, 1H), 6.44 (s, 2H), 7.30 (d, 1H), 7.59 (m, 1H), 7.64 (d, 1H), 7.76 (s, 1H), 8.35 (d, 1H), 9.37 (s, 1H); Mass Spectrum: M+H+ 408.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth (Celite®)
  2. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-17fe2a5dc7aa45a180d5bbb6a39b1aec
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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