Sodium Hydroxide → 1-Ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 490904Notes

Reaction equation

HRID 490904 reaction equation
[OH-].[Na+].[CH2:3]([N:5]1[C:9]2=[N:10][C:11]([CH3:26])=[C:12]([C:21]([O:23]CC)=[O:22])[C:13]([NH:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:8]2[CH:7]=[N:6]1)[CH3:4]>C(O)C>[CH2:3]([N:5]1[C:9]2=[N:10][C:11]([CH3:26])=[C:12]([C:21]([OH:23])=[O:22])[C:13]([NH:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:8]2[CH:7]=[N:6]1)[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57675194Ethyl 1-ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 576751871-Ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acidYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M-Sodium hydroxide solution (0.75 ml, 1.5 mmol) was added to Intermediate 59 (0.248 g, 0.75 mmol) in ethanol (2 ml), and the mixture was heated at reflux for 16 hours. The reaction mixture was concentrated, diluted with water (1 ml) and acidified with 2M-hydrochloric acid (0.75 ml) to precipitate a solid which was collected by filtration to afford Intermediate 60 (0.168 g). LCMS showed MH+=305; TRET=1.86 min.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with water (1 ml)
  5. customto precipitate a solid which
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-8761e89f4b694a87967e5c199e32c5a7
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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