HCID 70240736, compound → HCID 21191856, compound

HRID 2292763Notes

Reaction equation

HRID 2292763 reaction equation
[NH:1]([C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]([CH3:21])=[C:8]2[CH2:22][C:23]([NH:25]N)=[O:24])=[O:4])N>[Ni].CCO>[NH2:1][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]([CH3:21])=[C:8]2[CH2:22][C:23]([NH2:25])=[O:24])=[O:4]

Participants

4

Reactant 1

HCID 70240736HCID 70240736, compound

Product 1

HCID 21191856HCID 21191856, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Using the method described in Example 3, Part D, 40 mg (0.11 mmol) of 5-hydrazinocarbonyl-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide was hydrogenolized using approximately 1 g of Raney nickel in 50 mL of EtOH to give after chromatography on silica (gradient, CH2 Cl2 →8% MeOH/CH2Cl2) 17 mg (50% yield) of 5-aminocarbonyl-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide.

Sources & evidence

ORD record
ord-8a7000f83ccf4c26aa05b31d717a44de
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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