Hydrochloric Acid → HCID 86678163, compound

HRID 82027Notes

Reaction equation

HRID 82027 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[C:15]([I:16])=[N:14][N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[C:8]=2[N:9]=[C:10]([Cl:12])[CH:11]=1)=[O:5])C.[OH-].[Na+].Cl.O>O1CCOCC1>[Cl:12][C:10]1[CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]2[C:15]([I:16])=[N:14][N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[C:8]=2[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 866781586-chloro-3-iodo-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

Product 1

HCID 86678163HCID 86678163, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-chloro-3-iodo-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (25 g, 57 mmol) in 1,4-dioxane (200 mL) was added an aqueous sodium hyroxide solution (1M, 180 mL). The reaction mixture was stirred at room temperature for 7 hours and then an aqueous HCl solution (1M, 200 mL) was carefully added. Water (140 mL) was added, and after 5 minutes of stirring the precipitate was filtered, washed with water, cyclohexane and then dried to afford the title compound as a yellow solid (17.1 g, 73%).

Workup

  1. stirringafter 5 minutes of stirring the precipitate
  2. filtrationwas filtered
  3. washwashed with water, cyclohexane
  4. customdried

Sources & evidence

ORD record
ord-83ef0f158b294d1997d3149c76e46945
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Reaction notes

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