Sodium hydride → 4-(1-(4-((tert-butyl(dimethyl)silyl)oxy)cyclohexyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

HRID 2206124Notes

Reaction equation

HRID 2206124 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)=[N:10][NH:11][C:7]=2[CH:6]=[CH:5][N:4]=1.[H-].[Na+].CC1C=CC(S(O[CH:35]2[CH2:40][CH2:39][CH:38]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH2:37][CH2:36]2)(=O)=O)=CC=1>CN(C=O)C>[Si:42]([O:41][CH:38]1[CH2:37][CH2:36][CH:35]([N:11]2[C:7]3[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=3[C:9]([C:12]3[CH:13]=[CH:14][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][CH:17]=3)=[N:10]2)[CH2:40][CH2:39]1)([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1179882914-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamideHCID 131735826cis-4-((tert-Butyldimethylsilyl)oxy)cyclohexyl 4-methylbenzenesulfonate

Product 1

HCID 1317358374-(1-(4-((tert-butyl(dimethyl)silyl)oxy)cyclohexyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide (50.0 mg) obtained in Step A of Example 100 in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil, 7.89 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 4-((tert-butyl(dimethyl)silyl)oxy)cyclohexyl 4-methylbenzenesulfonate (76.0 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (52.8 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dc4a820004b24c08a083aeab64eb2bb4
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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