HCID 23508341, compound → HCID 23508359, compound

HRID 1883658Notes

Reaction equation

HRID 1883658 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:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27](=[O:29])[CH3:28])([O-])=O>CO.[Pd]>[NH2:1][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:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27](=[O:29])[CH3:28]

Participants

4

Reactant 1

HCID 23508341HCID 23508341, compound

Product 1

HCID 23508359HCID 23508359, compoundYield 68.1%

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-phenylacetamide (0.82 g, 1.7 mmole) in CH3OH (50 mL) in a Parr hydrogenation flask was added 10% Pd/C (0.50 g). The contents were shaken on a Parr shaker under H2 (50 psi) for 4 hours. The reaction suspension was filtered through celite and concentrated under vacuum. Purification on silica (CHCl3/CH3OH, 95:5) afforded the title compound (0.51 g, 68%) as an off-white solid: MS (ES) m/e 441 (M+H)+.

Workup

  1. filtrationThe reaction suspension was filtered through celite
  2. concentrationconcentrated under vacuum
  3. customPurification on silica (CHCl3/CH3OH, 95:5)

Sources & evidence

ORD record
ord-74b227c9b77f4f45b0f9e2ea7c837aae
Source dataset
uspto-grants-2004_07
Patent number
US06762201B1

Reaction notes

Loading…