Water → N-cyclohexyl-5-(2,5-dioxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-4-amine

HRID 1966827Notes

Reaction equation

HRID 1966827 reaction equation
Br[CH2:2][C:3]1([CH2:26][OH:27])[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:10]3[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:11]3=[N:12][CH:13]=2)[CH2:4]1.O.[OH-].[K+]>C(O)C>[CH:20]1([NH:19][C:9]2[C:10]3[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:11]=3[N:12]=[CH:13][C:8]=2[C:5]2[CH2:4][C:3]3([CH2:26][O:27][CH2:2]3)[O:7][N:6]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 66733284{5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazol-5-yl}methanol

Product 1

HCID 66732556N-cyclohexyl-5-(2,5-dioxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-4-amineYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{5-(Bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazol-5-yl}methanol (110 mg, 0.00025 mole) (example 20) was dissolved in ethanol (10 ml). Water (2 ml) was added followed by potassium hydroxide (20 mg, 0.00050 mole). The reaction mixture was stirred at refluxing temperature overnight. The solvent was removed under reduced pressure. Water was added and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product obtained was purified by column chromatography.

Workup

  1. temperatureat refluxing temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6736ea1bab604d2a871d6a18c831a878
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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