Tetrabutylammonium Fluoride → HCID 59278295, compound

HRID 1698132Notes

Reaction equation

HRID 1698132 reaction equation
[CH3:1][S:2]([NH:5][C:6]1(NS(C)(=O)=O)[CH:11]=[C:10]([CH2:12][NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])[CH:9]=[CH:8][NH:7]1)(=[O:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[C:10]([CH2:12][NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])[CH:9]=[CH:8][N:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86640800HCID 86640800, compound

Product 1

HCID 59278295HCID 59278295, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (2,2-bismethanesulfonylamino-pyridin-4-ylmethyl)-amide (36 mg, 0.069 mmol) in THF (1 mL) was added a 1 M solution of tetra-n-butylammonium fluoride (347 μL, 0.347 mmol) in THF and the mixture was warmed at reflux. After 1 hour, the mixture was quenched with saturated aqueous ammonium chloride (15 mL) and diluted with EtOAc (15 mL). The organic phase was separated and washed with NaHCO3 (10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane to afford the title compound as a solid.

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux
  3. customthe mixture was quenched with saturated aqueous ammonium chloride (15 mL)
  4. additiondiluted with EtOAc (15 mL)
  5. customThe organic phase was separated
  6. washwashed with NaHCO3 (10 mL), brine (10 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with a gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-968efb9f5c24466498e1013e9c6def73
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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