Hydrochloric Acid → HCID 86606798, compound

HRID 2376753Notes

Reaction equation

HRID 2376753 reaction equation
C([O:3][CH:4](OCC)[CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([N:9]=[C:10]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:11]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:12]2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:7]1)C.Cl>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[C:13]3[C:8](=[N:7][N:6]([CH2:5][CH:4]=[O:3])[CH:14]=3)[N:9]=[C:10]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:11]=2[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 684434952-(2,2-Diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Product 1

HCID 86606798HCID 86606798, compoundYield 65%

Conditions

Temperature
100 °C

Procedure

In a volumetric flask, 2-(2,2-diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (0.31 g, 0.6 mmol, obtained in example 73) and 1 N HCl (2.6 mL) were introduced. The mixture was heated to 100° C. for 1 hour. It was allowed to cool, adjusted to pH=7 and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity eluent, to afford 166 mg of the title compound (yield: 65%).

Workup

  1. temperatureto cool
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product obtained
  6. customwas purified by chromatography on silica gel
  7. temperatureof increasing polarity eluent

Sources & evidence

ORD record
ord-cc9c46ecd5d54c649cdb78160af0fb47
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Reaction notes

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