HCID 10785116, compound → HCID 11792248, compound

HRID 1069624Notes

Reaction equation

HRID 1069624 reaction equation
[NH:1]([C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:23][C:24]([NH2:26])=[O:25])=[C:9]([CH3:22])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)N>C(O)C.[Ni]>[NH2:1][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:23][C:24]([NH2:26])=[O:25])=[C:9]([CH3:22])[N:10]2[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 10785116HCID 10785116, compound

Product 1

HCID 11792248HCID 11792248, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 230mg (0.63 mmol) of 4-(2-hydrazino-2-oxoethoxy)-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide and 300 mg of Raney Ni in 40 mL of ethanol was heated to maintain reflux for 4 hours. The mixture was cooled the EtOH poured off the catalyst, and the catalyst washed twice with methylene chloride. The combined solvents were filtered, concentrated and the residue chromatographed on silica gel and on eluting with 10% MeOH/EtOAc, 25 mg (11% yield) of 4-(2-amino-2-oxoethoxy)-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide were obtained. This material melted at 190-207° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 4 hours
  4. additionpoured off the catalyst
  5. washthe catalyst washed twice with methylene chloride
  6. filtrationThe combined solvents were filtered
  7. concentrationconcentrated
  8. customthe residue chromatographed on silica gel
  9. washon eluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-48e63edd544342bc8db3c3d3baf8887b
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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