HCID 66732990, compound → HCID 66732777, compound

HRID 1966823Notes

Reaction equation

HRID 1966823 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:20]3[CH2:24][C:23]4([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[O:22][N:21]=3)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:20]3[CH2:24][C:23]4([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[O:22][N:21]=3)[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][C:16](=[O:19])[CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 66732990HCID 66732990, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 66732777HCID 66732777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

4-{[1-Ethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]amino}cyclohexanol (100 mg, 0.251 mmol) (example 9) was dissolved in dichloromethane and the reaction mixture was cooled up to 5° C. Pyridinium chlorochromate (108 mg, 0.502 mmol) was added and the reaction mixture was stirred for about 5 minutes at the same temperature. It was warmed to room temperature and stirred at room temperature for about 16 h. Dilution was done with dichloromethane and filtration was done using celite. The organic layers were combined, concentrated and purified by preparative thin layer chromatography by using ethyl acetate.

Workup

  1. temperatureIt was warmed to room temperature
  2. stirringstirred at room temperature for about 16 h
  3. filtrationDilution was done with dichloromethane and filtration
  4. concentrationconcentrated
  5. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-1b457ef2412a4783af6ef91c9c14f587
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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