Methanol → HCID 178499647, compound

HRID 1952355Notes

Reaction equation

HRID 1952355 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[N:2]1.[CH3:14]O>Cl>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 178525255HCID 178525255, compound

Product 1

HCID 178499647HCID 178499647, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 1H-pyrazolo[3,4-b]pyridin-3-ylacetic acid (92 mg, 0.520 mmol) in methanol (4 mL) was bubbled in HCl gas for 2 minutes and the resulting solution was allowed to stand for a further 10 minutes. After this time, the solution was concentrated in vacuo and the resulting residue was partitioned between aqueous NaHCO3 (10 mL) and ethyl acetate (2×10 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to provide the title compound. LRMS (M+1): 192.0.

Workup

  1. concentrationAfter this time, the solution was concentrated in vacuo
  2. customthe resulting residue was partitioned between aqueous NaHCO3 (10 mL) and ethyl acetate (2×10 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-77d3ff586e91461981571b5880fd712e
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

Loading…