Hydrochloric Acid → HCID 66732673, compound

HRID 1966848Notes

Reaction equation

HRID 1966848 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[CH2:23][C:17]4([CH2:20][CH:19]([C:21]#N)[CH2:18]4)[O:16][N:15]=3)=[CH:12][N:11]=[C:10]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:29].[K+].Cl.[OH2:32]>C(O)C>[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[CH2:23][C:17]4([CH2:18][CH:19]([C:21]([OH:32])=[O:29])[CH2:20]4)[O:16][N:15]=3)=[CH:12][N:11]=[C:10]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 66732752HCID 66732752, compound

Product 1

HCID 66732673HCID 66732673, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-[4-(Cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carbonitrile (300 mg, 0.00079 mole) (example 9) was dissolved in ethanol (10 ml). Aqueous potassium hydroxide (178 mg, 0.0031 mole) was added and reaction mixture was refluxed for about 3-4 hrs. Ethanol was evaporated off and reaction mixture was diluted with water, acidifed with dilute hydrochloric acid to pH of about 6. It was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure to give crude compound. The title compound was purified by preparative thin layer chromatography.

Workup

  1. customreaction mixture
  2. temperaturewas refluxed for about 3-4 hrs
  3. customEthanol was evaporated off
  4. customreaction mixture
  5. extractionIt was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto give crude compound
  10. customThe title compound was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-a3585d67b3f34729bc3e6c368b950de8
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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