Hydrazine → HCID 11999119, compound

HRID 2102756Notes

Reaction equation

HRID 2102756 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=4)[C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=4)[C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH2:14]2)=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 11999118HCID 11999118, compound

Product 1

HCID 11999119HCID 11999119, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (4-nitro-phenyl)-amide (0.15 g, 0.28 mmol) (from Example 76a supra) in ethanol (15 mL) was added Rani-nickel, followed by the addition of hydrazine (35 mg, 0.84 mmol) (Aldrich). The mixture was stirred at room temperature for 20 minutes. The crude was filtered through the celite pad. The filtrate was concentrated and the residue was purified by chromatography to give rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (4-amino-phenyl)-amide as a white solid (Yield 90 mg, 64%).

Workup

  1. filtrationThe crude was filtered through the celite pad
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-7238fccaf50c4275bfa13e696848bc01
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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