Sodium Hydroxide → 1-isopropyl-6-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1909213Notes

Reaction equation

HRID 1909213 reaction equation
[OH-].[Na+].[CH:3]([N:6]1[C:10]2[N:11]=[C:12]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH:13]=[C:14]([C:15]([O:17]CC)=[O:16])[C:9]=2[CH:8]=[N:7]1)([CH3:5])[CH3:4]>CCO>[CH:3]([N:6]1[C:10]2[N:11]=[C:12]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH:13]=[C:14]([C:15]([OH:17])=[O:16])[C:9]=2[CH:8]=[N:7]1)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68294946ethyl 1-isopropyl-6-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 682954841-isopropyl-6-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Aqueous NaOH (0.193 g, 4.833 mmol) was added to a solution of ethyl 1-isopropyl-6-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (0.32 g, 0.966 mmol) in EtOH (6 mL) and stirred at 60° C. for 1 h. After completion of the reaction, ethanol was removed under reduced pressure and it was acidified using 10% citric acid solution. Extraction was carried out using DCM; the combined organic layers were washed with water, brine; dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure to give the desired compound (0.2 g, 64.9%).

Workup

  1. customwas removed under reduced pressure and it
  2. extractionExtraction
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0dc174ba9b2f4878a1d0c17ee5998f6b
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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