Hydrazine → 2-ethyl-5-(4-hydrazino-4-oxobutoxy)-1-(phenylmethyl)-1H-indole-3-acetamide

HRID 1069613Notes

Reaction equation

HRID 1069613 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([CH2:25][CH3:26])=[C:12]2[CH2:27][C:28]([NH2:30])=[O:29])C.[NH2:32][NH2:33]>C(O)C.O>[CH2:25]([C:13]1[N:14]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:15]2[C:11]([C:12]=1[CH2:27][C:28]([NH2:30])=[O:29])=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([NH:32][NH2:33])=[O:3])=[CH:17][CH:16]=2)[CH3:26]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 105501624-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

Product 1

HCID 211918472-ethyl-5-(4-hydrazino-4-oxobutoxy)-1-(phenylmethyl)-1H-indole-3-acetamideYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 211 mg (0.05 mmol) of [4-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1-H-indol-5-yl]oxy]butanoic acid ethyl ester and 1 mL of hydrazine in 5 mL of ethanol was heated to maintain reflux for 5 hours. The mixture was diluted with water, extracted with ethyl acetate, the ethyl acetate washed with brine, dried (MgSO4), and concentrated at reduced pressure. The residue was stirred with MeOH and the insoluble material filtered to give 177 mg (37% yield) of 2-ethyl-5-(4-hydrazino-4-oxobutoxy)-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 176-179° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 5 hours
  4. extractionextracted with ethyl acetate
  5. washthe ethyl acetate washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated at reduced pressure
  8. filtrationthe insoluble material filtered

Sources & evidence

ORD record
ord-7f54d14765c446938db716a34c9755c6
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

Loading…