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

HRID 1501582Notes

Reaction equation

HRID 1501582 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-4c89b5d6a61641e49ffed73d3e7203bc
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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