Hydrochloric Acid → HCID 69183135, compound

HRID 2373235Notes

Reaction equation

HRID 2373235 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:26][O:27][CH3:28])=[C:10](/[CH:19]=[CH:20]/[C:21]([O:23]CC)=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[OH-].[Na+].Cl>CCO.[Cl-].[Na+].O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:26][O:27][CH3:28])=[C:10](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86602404HCID 86602404, compound

Product 1

HCID 69183135HCID 69183135, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of ethyl (2E)-3-[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]acrylate (30 mg) in EtOH (2 ml) was added 1N aqueous NaOH (0.16 ml) and the mixture was stirred at 40° C. for 1 hour. After cooling, the reaction mixture was acidified to pH3-4 by adding 1N HCl (0.16 ml). The mixture was diluted with brine and extracted with CHCl3. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography eluting with a mixture of MeOH and CHCl3 (1:10). The residue was recrystallized from EtOAc-n-hexane to give (2E)-3-[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]acrylic acid (15 mg) as a colorless crystal.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography
  6. washeluting with a mixture of MeOH and CHCl3 (1:10)
  7. customThe residue was recrystallized from EtOAc-n-hexane

Sources & evidence

ORD record
ord-56f56298e9cc4e5593d72a7ac779ab4a
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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