Sodium Hydroxide → HCID 89544017, compound

HRID 1522523Notes

Reaction equation

HRID 1522523 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([O:17]C)=[O:16])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]3[CH2:14][CH2:13]3)[C:6]=2[N:7]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]3[CH2:13][CH2:14]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89467172HCID 89467172, compound

Product 1

HCID 89544017HCID 89544017, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 6-chloro-1-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (370 mg, 1.393 mmol) in ethanol (30 mL) was added 1N sodium hydroxide (1.393 mL, 1.393 mmol) and heated at reflux for 2 hours. The solvent was removed in vacuo, the residue dissolved in 20 mL of water, and acidified with acetic acid. The contents were extracted with EtOAc (4×30 mL). The combined organic layers were washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo. The product was collected as 297 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.77-1.43 (m, 4 H), 2.55 (s, 3 H), 3.63-4.15 (m, 1 H), 7.52 (s, 1 H), 14.18 (br. s., 1 H). LCMS(ES) [M+H]+252.4

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in 20 mL of water
  5. extractionThe contents were extracted with EtOAc (4×30 mL)
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe product was collected as 297 mg

Sources & evidence

ORD record
ord-0d09ceb2990443c38bb54b1fe42ce29d
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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