Hydrochloric Acid → HCID 178469361, compound

HRID 489417Notes

Reaction equation

HRID 489417 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH:19](OC)[O:20]C)[NH:11][C:10]2=[N:24][NH:25][CH:26]=[C:9]12.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH:19]=[O:20])[NH:11][C:10]2=[N:24][NH:25][CH:26]=[C:9]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178469335HCID 178469335, compound

Product 1

HCID 178469361HCID 178469361, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(2-chlorophenyl)-6-dimethoxymethyl-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxylate (463 mg) in tetrahydrofuran (5 ml) was added 1 N hydrochloric acid (10 ml) and the mixture was stirred at room temperature for 6 hours. To the reaction mixture was added a saturated aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1)) to give the title compound (290 mg) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1))

Sources & evidence

ORD record
ord-4691eaec941f49f185b9fd022d08f50e
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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