Water → 4-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 1966806Notes

Reaction equation

HRID 1966806 reaction equation
[OH-].[Na+].[CH:3]1([NH:9][C:10]2[C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][N:13]=[C:12]3[N:21]([CH2:24][CH3:25])[N:22]=[CH:23][C:11]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.O>C(O)C>[CH:3]1([NH:9][C:10]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][N:13]=[C:12]3[N:21]([CH2:24][CH3:25])[N:22]=[CH:23][C:11]=23)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 10448469ethyl 4-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 586293764-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide solution (4.09 gm in 20 ml water) was added to a solution of ethyl 4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (9.32 gm, 0.0294 mole) (example 4) in ethanol. The reaction mixture was stirred for about 14 h at room temperature and then warmed for about 1 h at 60° C. Water was added and the reaction mixture was extracted with ethyl acetate. Aqueous layer was acidified by using hydrochloric acid (2N) to pH of about 4-5. White solid, which was obtained, was filtered and dried in vacuo.

Workup

  1. temperaturewarmed for about 1 h at 60° C
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customWhite solid, which was obtained
  4. filtrationwas filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-25fea81309c14e6aa1867a43697239f4
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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