Sodium Hydroxide → HCID 89444908, compound

HRID 1522531Notes

Reaction equation

HRID 1522531 reaction equation
[CH:1]1([N:4]2[C:8]3[N:9]=[C:10]([CH:18]4[CH2:20][CH2:19]4)[CH:11]=[C:12]([C:13]([O:15]CC)=[O:14])[C:7]=3[C:6]([CH3:21])=[N:5]2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([N:4]2[C:8]3[N:9]=[C:10]([CH:18]4[CH2:19][CH2:20]4)[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:7]=3[C:6]([CH3:21])=[N:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89444869HCID 89444869, compound

Product 1

HCID 89444908HCID 89444908, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1,6-dicyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (310 mg, 1.086 mmol) in ethanol (30 mL) was added sodium hydroxide (4.35 mL, 4.35 mmol) and the mixture heated at reflux for 2 hours. The solvent was removed in vacuo, the residue suspended in water (20 mL), and acidified by addition of acetic acid. The contents were extracted with EtOAc (4×30 mL). The combined EtOAc extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The product was collected as 250 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.88-1.31 (m, 8 H), 2.21-2.42 (m, 1 H), 3.83 (m, J=7.39, 7.39, 3.79, 3.66 Hz, 1 H), 7.44 (s, 1 H), 13.72 (br. s., 1 H). LCMS(ES) [M+H]+ 258.2

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. additionacidified by addition of acetic acid
  5. extractionThe contents were extracted with EtOAc (4×30 mL)
  6. washThe combined EtOAc extracts were washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe product was collected as 250 mg

Sources & evidence

ORD record
ord-3253b9a0045f45b8a1b6971de92e68b7
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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