Sodium Hydroxide → 1-Amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522444Notes

Reaction equation

HRID 1522444 reaction equation
[NH2:1][N:2]1[C:6]2[N:7]=[C:8]([CH:16]3[CH2:18][CH2:17]3)[CH:9]=[C:10]([C:11]([O:13]CC)=[O:12])[C:5]=2[CH:4]=[N:3]1.[OH-].[Na+]>C(O)C>[NH2:1][N:2]1[C:6]2[N:7]=[C:8]([CH:16]3[CH2:17][CH2:18]3)[CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:5]=2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67124432Ethyl 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671242951-Amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (100 mg, 0.406 mmol) in ethanol (10 mL) was added sodium hydroxide (1 ml, 0.406 mmol), and the mixture stirred at room temperature for 2 h. The solvent was removed in vacuo, and the residue diluted with EtOAc (30 mL) and water (20 mL). The reaction mixture was acidified to pH 3 with citric acid. The phases were separated and the aq. phase extracted with EtOAc (4×20 mL). The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The final product was collected as 0.075 g (84%). LCMS E-S (M+H)=219.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00-1.13 (m, 4 H), 2.27-2.45 (m, 1 H), 6.36 (s, 2 H), 7.60 (s, 1 H), 8.06 (s, 1 H), 13.81 (br. s., 1 H).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with EtOAc (30 mL) and water (20 mL)
  3. customThe phases were separated
  4. extractionthe aq. phase extracted with EtOAc (4×20 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe final product was collected as 0.075 g (84%)

Sources & evidence

ORD record
ord-428693c697ff445d86f9822570b36cab
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…