Hydrazine → HCID 178430817, compound

HRID 1433164

Reaction equation

HRID 1433164 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:22]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][C:32]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[NH:29][CH:28]=[C:27]3[CH3:41])=O)=[CH:18][N:19](C)C)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:42]N>CCO>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[C:22]([C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][C:32]=3[O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:29][CH:28]=[C:27]4[CH3:41])=[N:42][NH:19][CH:18]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 690605914-[1-(6-Benzyloxy-3-methyl-1H-indole-5-carbonyl)-2-dimethylamino-vinyl]-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 178430817HCID 178430817, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[1-(6-benzyloxy-3-methyl-1H-indole-5-carbonyl)-2-dimethylamino-vinyl]-piperazine-1-carboxylic acid benzyl ester (0.158 g, 0.29 mmol) and hydrazine (0.75 ml, 15.5 mmol) in EtOH was refluxed for 1 hour, after which time the reaction had gone to completion. The solvent was removed in vacuo and the product purified by column chromatography in hexane/EtOAc (1:1) to afford an off-white solid (0.0445 g, 30%). LC/MS: RT=2.713 min. 522 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product purified by column chromatography in hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-475cc5156b894e6887fecb275cdbc5af
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Linked notes

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