Sodium Hydroxide → HCID 23400329, compound

HRID 1062580Notes

Reaction equation

HRID 1062580 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:9]([C:11]#[N:12])[CH:10]=[C:5]2[C:4]([CH3:20])=[N:3]1.[OH-:21].[Na+]>OS(O)(=O)=O>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:9]([C:11]([NH2:12])=[O:21])[CH:10]=[C:5]2[C:4]([CH3:20])=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22282146HCID 22282146, compound

Product 1

HCID 23400329HCID 23400329, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

1,3-Dimethyl-6-[2-(pyrrolidin-1-yl)ethyl]-1H-pyrazolo [3,4-b]pyridine-5-carbonitrile was dissolved in concentrated H2SO4 (55 mL) and the solution stirred at 60° C. for 2 days. The mixture was cooled to 0° C., treated with 6N NaOH to pH 14, and extracted with ethyl acetate. The organic extract was evaporated under reduced pressure and the residue washed with ether to give 1,3-dimethyl-6-[2-(pyrrolidin-1-yl)ethyl)-1H-pyrazolo [3,4-b]pyridine-5-carboxamide (2.5 g).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. customwas evaporated under reduced pressure
  5. washthe residue washed with ether

Sources & evidence

ORD record
ord-84543aec2189418cab48bb18132e76ce
Source dataset
uspto-grants-2005_11
Patent number
US06962926B2

Reaction notes

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