HCID 57834996, compound → HCID 57834973, compound

HRID 730582Notes

Reaction equation

HRID 730582 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16](=O)[C:17](=[O:31])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>NN.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][C:17](=[O:31])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57834996HCID 57834996, compound

Product 1

HCID 57834973HCID 57834973, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 9321HydrazineSolvent

Procedure

4-[1-(3-Fluoro-benzyl)-2,3-dioxo-2,3-dihydro-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (930 mg) was dissolved in 17 ml each of hydrazine and ethanol, and the solution was heated at 110° C. for 16 hours. The reaction was cooled and partitioned between water and ethyl acetate, and the organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography to afford 146 mg of 4-[1-(3-fluoro-benzyl)-2-oxo-2,3-dihydro-1H-indol-4-yl]-piperidine-1-carboxylic acid tert-butyl ester. MS: 423 (M−H)−.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between water and ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-d056d7b75b564026a84b61c93181848e
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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