HCID 23508344, compound → HCID 69758887, compound

HRID 1883657Notes

Reaction equation

HRID 1883657 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[N:11]([CH3:23])[CH2:12][C:13]2[N:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:6][C:5]=1[CH2:25][N:26](C)[C:27](OCC1C=CC=CC=1)=O)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:11]([CH3:23])[CH2:12][C:13]2[N:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:24])=[CH:6][C:5]=1[CH2:25][NH:26][CH3:27]

Participants

4

Reactant 1

HCID 23508344HCID 23508344, compound

Product 1

HCID 69758887HCID 69758887, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[(2-nitro-5-{N-methyl-N-[(1-methylindol-2-yl)methyl]carbamoyl}phenyl)methyl]-N-methyl(phenylmethoxy)carboxamide (6.1 g, 12.2 mmole) in CH3OH (50 mL) contained in a Parr hydrogenation flask was added a 0.75 g of 10% Pd/C. The contents were shaken on a Parr shaker under H2 (50 psi) for 6 hours. The suspension was filtered through celite and concentrated under vacuum. Purification on silica [CHCl3/CH3OH (containing 5% NH4OH), 9:1] afforded the title compound (3.40 g, 83%) as a viscous yellow oil: MS (ES) m/e 337 (M+H)+.

Workup

  1. filtrationThe suspension was filtered through celite
  2. concentrationconcentrated under vacuum
  3. customPurification on silica [CHCl3/CH3OH (containing 5% NH4OH), 9:1]

Sources & evidence

ORD record
ord-0e9199dbe2b14e7991c2a90da69caafe
Source dataset
uspto-grants-2004_07
Patent number
US06762201B1

Reaction notes

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