Sodium Hydroxide → HCID 178434435, compound

HRID 715028Notes

Reaction equation

HRID 715028 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=3)[C:14]([O:16]CC)=[O:15])[CH:9]=2)[NH:4][N:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=3)[C:14]([OH:16])=[O:15])[CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468820HCID 178468820, compound

Product 1

HCID 178434435HCID 178434435, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 3-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate (119) (10 mg, 0.142, 1 eq) in ethanol (5 mL) was added 4N sodium hydroxide solution (4 mL) and the reaction mixture was stirred at room temperature for 4 hrs. After completion of the reaction the solvents were distilled off and diluted with water and the pH adjusted to 4 and extracted into chloroform. The organic layer was dried over sodium sulphate and the solvents were removed to get the compound 3-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzoic acid 120 and this was further titrated with hexane and diethyl ether to get 15 mg of 120.

Workup

  1. customAfter completion of the reaction the solvents
  2. distillationwere distilled off
  3. additiondiluted with water
  4. extractionextracted into chloroform
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. customthe solvents were removed

Sources & evidence

ORD record
ord-254301658c0c488791c2937bdfc76ac5
Source dataset
uspto-grants-2015_11
Patent number
US09187473B2

Reaction notes

Loading…