Hydrazine hydrate (1:1) → HCID 23145252, compound

HRID 13271Notes

Reaction equation

HRID 13271 reaction equation
O.NN.[N+:4]([C:7]1[CH:8]=[C:9]([CH:42]=[CH:43][C:44]=1[N+:45]([O-])=O)[O:10][C:11]1[C:12]([CH:34]2[CH2:38][CH2:37][CH2:36][N:35]2[C:39](=[O:41])[CH3:40])=[CH:13][C:14]2[N:18]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[N:16][C:15]=2[CH:33]=1)([O-])=O>[Ni].C(O)C>[NH2:4][C:7]1[CH:8]=[C:9]([CH:42]=[CH:43][C:44]=1[NH2:45])[O:10][C:11]1[C:12]([CH:34]2[CH2:38][CH2:37][CH2:36][N:35]2[C:39](=[O:41])[CH3:40])=[CH:13][C:14]2[N:18]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[N:16][C:15]=2[CH:33]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23145382HCID 23145382, compound

Product 1

HCID 23145252HCID 23145252, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

0.030 ml of hydrazine monohydrate and 20 mg of developed Raney nickel catalyst were added to an ethanol (1 ml) solution of 72 mg of 1-(2-(6-(3,4-dinitro-phenoxy)-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone, and the reaction liquid was stirred at room temperature for 2 hours. The catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1) to obtain the entitled compound as a brown oily substance.

Workup

  1. customthe reaction liquid
  2. customThe catalyst was removed through filtration through Celite
  3. customthe solvent was evaporated away under reduced pressure
  4. customThe resulting residue was purified
  5. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)
  6. customto obtain the entitled compound as a brown oily substance

Sources & evidence

ORD record
ord-98daf3fcd5d74a3a9b8c37a03e04a341
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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