Bromocyclopentane → HCID 66733050, compound

HRID 1966835Notes

Reaction equation

HRID 1966835 reaction equation
[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]([C:19]3[CH2:23][C:22]4([CH2:27][CH2:26][CH2:25][CH2:24]4)[O:21][N:20]=3)=[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:6]=2[CH:5]=[N:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH:34]1(Br)[CH2:38][CH2:37][CH2:36][CH2:35]1>C(#N)C>[CH:34]1([N:16]2[CH2:15][CH2:14][CH:13]([NH:12][C:11]3[C:6]4[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]=4[N:8]=[CH:9][C:10]=3[C:19]3[CH2:23][C:22]4([CH2:27][CH2:26][CH2:25][CH2:24]4)[O:21][N:20]=3)[CH2:18][CH2:17]2)[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 66732712HCID 66732712, compound

Product 1

HCID 66733050HCID 66733050, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-N-piperidin-4-yl-1H-pyrazolo[3,4-b]pyridin-4-amine (70 mg, 0.0018 mole) (example 31) was taken in acetonitrile and potassium carbonate (126 mg, 0.0009 mole) and cyclopentyl bromide (0.020 ml, 0.0002 mole) were added. The reaction mixture was stirred at refluxing temperature overnight. Acetonitrile was removed and water was added to the residue. Extraction was done with ethyl acetate and washings were done with brine. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure and the crude product was purified by preparative thin layer chromatography.

Workup

  1. temperatureat refluxing temperature overnight
  2. customAcetonitrile was removed
  3. additionwater was added to the residue
  4. extractionExtraction
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customthe crude product was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-4a263d892a494631bec435ee934fa306
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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