Sodium hydride → 4-(1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

HRID 2206175Notes

Reaction equation

HRID 2206175 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[CH2:44][CH2:43][C:38]3([O:42][CH2:41][CH2:40][O:39]3)[CH2:37][CH2:36]2)(=O)=O)=CC=1>CN(C=O)C>[O:39]1[C:38]2([CH2:43][CH2:44][CH:35]([N:11]3[C:7]4[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=4[C:9]([C:12]4[CH:13]=[CH:14][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][CH:17]=4)=[N:10]3)[CH2:36][CH2:37]2)[O:42][CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)HCID 1179882914-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

Product 1

HCID 1179879144-(1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamideYield 38.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide (500 mg) obtained in Step A of Example 100 in DMF (8 mL) was added sodium hydride (60% dispersion in mineral oil, 131 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 1,4-dioxaspiro[4.5]dec-8-yl 4-methylbenzenesulfonate (1.03 g), and the mixture was stirred overnight at 60° C. The reaction mixture was extracted with ethyl acetate and water. 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 (ethyl acetate/methanol) to give the title compound (283 mg).

Workup

  1. stirringthe mixture was stirred overnight at 60° C
  2. extractionThe reaction mixture was extracted with ethyl acetate and water
  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 (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-83381e2d59cd451dbd0f014e6fc64eab
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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