Water → HCID 67209443, compound

HRID 402489Notes

Reaction equation

HRID 402489 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:8][C:9]=2[CH3:11])[N:4]([CH3:19])[N:3]=1.O.[Li+].[OH-]>O1CCOCC1>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][C:9]=2[CH3:11])[N:4]([CH3:19])[N:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 67209453Acetic acid, 2-[(3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy]-, ethyl ester

Product 1

HCID 67209443HCID 67209443, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Ethyl 2-((3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetate in dioxane (5 ml) were added H2O (2.5 ml) and LiOH (111 mg, 4.65 mmol). After 2 h, more water was added and the mixture extracted with CH2Cl2. Then, the aqueous phase was acidified by drop wise addition of conc. HCl until the product precipitated. The title compound (580 mg, 98%) was filtered off and dried under reduced pressure. [1H-NMR (DMSO-d6, 400 MHz) δ 6.62 (s, 1H), 4.98 (s, 2H) 3.84 (s, 3H), 2.61 (s, 3H); HPLC-MS RtJ=0.81 min; [M+H]+=255.9, 258.0]

Workup

  1. extractionthe mixture extracted with CH2Cl2
  2. additionThen, the aqueous phase was acidified by drop wise addition of conc. HCl until the product
  3. customprecipitated
  4. filtrationThe title compound (580 mg, 98%) was filtered off
  5. customdried under reduced pressure
  6. custom[1H-NMR (DMSO-d6, 400 MHz) δ 6.62 (s, 1H), 4.98 (s, 2H) 3.84 (s, 3H), 2.61 (s, 3H); HPLC-MS RtJ=0.81 min; [M+H]+=255.9, 258.0]

Sources & evidence

ORD record
ord-801b04a656ff4087813d25b7027b884a
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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