Water → HCID 178469152, compound

HRID 1909220Notes

Reaction equation

HRID 1909220 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[Cl:19]NC(=O)CCC(N)=O.O.C(OCC)(=O)C>CN(C=O)C>[Cl:19][C:3]1[C:2]([OH:1])=[N:7][C:6]2[N:8]([CH:11]([CH3:13])[CH3:12])[N:9]=[CH:10][C:5]=2[C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 15238416N-chlorosuccinamideHCID 178469345HCID 178469345, compound

Product 1

HCID 178469152HCID 178469152, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 6-hydroxy-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (1.3 g, 5.2 mmol) in DMF (7 mL), N-chlorosuccinamide (1.11 g, 8.35 mmol) was added. The resulting reaction mixture was stirred at 60° C. for 1 h. On completion of reaction, water was added to it and extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to obtain the desired intermediate (1 g, 69.9%).

Workup

  1. customThe resulting reaction mixture
  2. additionwas added to it and extraction
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customSolvent was removed under reduced pressure and residue
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9fa4f1cc6d4467da90884ecd9c5c658
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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