Hydrochloric Acid → HCID 67209460, compound

HRID 402475Notes

Reaction equation

HRID 402475 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:9][CH:10]=[C:5]2[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:3]1.[Li+].[OH-].Cl>C1COCC1.C(OCC)C>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][CH:10]=[C:5]2[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67210036HCID 67210036, compound

Product 1

HCID 67209460HCID 67209460, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Ethyl 2-(1-methyl-3-phenyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)acetate (0.33 g, 1.059 mmol) and aqueous LiOH (0.446 g, 10.599 mmol in 3.0 mL H2O) in THF (3.0 mL) was stirred at rt for 6 h. The reaction mixture was neutralized with diluted HCl and diluted with diethyl ether. The organic layer was extracted with water and brine and dried over anhydrous Na2SO4. Concentration of the organic layer furnished the crude product as a white solid. The crude product was purified by column chromatography (eluent: 75% EtOAc in hexane) to yield the title compound as a white solid (0.291 g, 97%). [1H-NMR (CDCl3, 300 MHz) δ 8.21 (d, 1H), 7.92-7.84 (m, 2H), 7.52-7.35 (m, 3H), 6.77 (d, 1H), 5.05 (s, 2H), 4.02 (s, 3H); HPLC RtA=4.315 min (97%); LCMS RtC=0.389 min; [M+H]+=283.9]

Workup

  1. extractionThe organic layer was extracted with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customConcentration of the organic layer furnished the crude product as a white solid
  4. customThe crude product was purified by column chromatography (eluent: 75% EtOAc in hexane)

Sources & evidence

ORD record
ord-690d784d5fe4487fae3430a5681e6e1c
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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