Lithium Hydroxide → [3-(3,5-Dimethoxy-phenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy]-acetic acid

HRID 402499Notes

Reaction equation

HRID 402499 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][C:16]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:17][C:18]=3[CH3:20])[N:13]([CH3:28])[N:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Li+].[OH-]>O1CCOCC1.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][C:16]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][C:18]=3[CH3:20])[N:13]([CH3:28])[N:12]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67209497HCID 67209497, compound

Product 1

HCID 67209308[3-(3,5-Dimethoxy-phenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy]-acetic acidYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-((3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetate (910 mg, 2.36 mmol) in dioxane (10 ml) and water (10 ml) was added LiOH (113 mg, 4.72 mmol) and the reaction mixture stirred at rt for 72 h. Then, water was added and the mixture extracted with CH2Cl2. The aqueous phase was then adjusted to pH ˜2 with aqueous 2M HCl. The resulting precipitate was then filtered off, washed with H2O and dried under vacuum to furnish 620 mg (74%) of the title compound. [1H-NMR (DMSO-d6, 600 MHz): δ 6.70 (br d, 2H), 6.55 (br s, 1H), 6.44 (s, 1H), 4.49 (s, 2H), 3.91 (s, 3H), 3.78 (s, 6H), 2.50 (s, 3H); UPLC-MS RtJ=0.93 min; [M+H]+=358.1]

Workup

  1. extractionthe mixture extracted with CH2Cl2
  2. filtrationThe resulting precipitate was then filtered off
  3. washwashed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-93d2d74f55194f1abf2f23e92c3d2f82
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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