Sodium periodate → HCID 59278166, compound

HRID 559642Notes

Reaction equation

HRID 559642 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1.I([O-])(=O)(=O)=[O:32].[Na+]>CO>[CH3:1][S:2]([C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1)=[O:32]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 45137394HCID 45137394, compound

Product 1

HCID 59278166HCID 59278166, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-1-(2-methylsulfanyl-pyridin-4-yl)-propyl]-amide (0.10 mg, 0.24 mmol) in MeOH (5 mL) was added an aqueous solution of sodium periodate (51 mg, 0.24 mmol). After 1.5 hours, a solid precipitated and additional MeOH (3 mL) was added. After 5 days, mixture was concentrated and partitioned between water (5 mL) and EtOAc (50 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by reversed-phase HPLC (Sunfire PrepC 18 OBD 5 mM 30×150 mm column) eluting with a gradient of 15-75% acetonitrile in water (0.1% TFA). The fractions from the column were concentrated to remove acetonitrile, made basic with saturated aqueous sodium bicarbonate and extracted with EtOAc. The organic phase was washed with brine, dried over sodium sulfate and concentrated to afford the title compound as a white solid.

Workup

  1. customa solid precipitated
  2. additionadditional MeOH (3 mL) was added
  3. waitAfter 5 days
  4. concentrationmixture was concentrated
  5. custompartitioned between water (5 mL) and EtOAc (50 mL)
  6. customThe organic phase was separated
  7. extractionthe aqueous layer was extracted with EtOAc (20 mL)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by reversed-phase HPLC (Sunfire PrepC 18 OBD 5 mM 30×150 mm column)
  12. washeluting with a gradient of 15-75% acetonitrile in water (0.1% TFA)
  13. concentrationThe fractions from the column were concentrated
  14. customto remove acetonitrile
  15. extractionextracted with EtOAc
  16. washThe organic phase was washed with brine
  17. dry with materialdried over sodium sulfate
  18. concentrationconcentrated

Sources & evidence

ORD record
ord-5bdffef9fd814f89b461e36916cbd67c
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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