Formaldehyde → HCID 59278099, compound

HRID 559643Notes

Reaction equation

HRID 559643 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([NH:10][C:11]([C:13]2[C:14]3[CH:21]=[N:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[C:15]=3[CH:16]=[N:17][CH:18]=2)=[O:12])[CH2:8][CH3:9])[CH2:3][CH2:2]1.C=O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:31][N:1]1[CH2:6][CH2:5][CH:4]([CH:7]([NH:10][C:11]([C:13]2[C:14]3[CH:21]=[N:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[C:15]=3[CH:16]=[N:17][CH:18]=2)=[O:12])[CH2:8][CH3:9])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59278379HCID 59278379, compound

Product 1

HCID 59278099HCID 59278099, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (1-piperidin-4-yl-propyl)-amide (0.10 mg, 0.26 mmol) and 37% aqueous formaldehyde (157 μL, 2.1 mmol) in MeOH (3 mL) was added sodium triacetoxyborohydride (83 mg, 0.39 mmol). After 2 hours, the reaction was quenched with saturated aqueous sodium bicarbonate (5 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by reversed-phase HPLC chromatography (Sunfire PrepC18 OBD 5 mM 30×150 mm column) eluting with a gradient of 5-75% acetonitrile in water (0.1% TFA). The fractions from the column were concentrated to remove acetonitrile, made basic with saturated aqueous sodium carbonate and extracted with EtOAc. The organic layer was dried and concentrated to afford the title compound.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate (5 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by reversed-phase HPLC chromatography (Sunfire PrepC18 OBD 5 mM 30×150 mm column)
  7. washeluting with a gradient of 5-75% acetonitrile in water (0.1% TFA)
  8. concentrationThe fractions from the column were concentrated
  9. customto remove acetonitrile
  10. extractionextracted with EtOAc
  11. customThe organic layer was dried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-9b58b20164cb4ef2a15ca129f619b739
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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