Benzenesulfonyl chloride → HCID 67953998, compound

HRID 1916868Notes

Reaction equation

HRID 1916868 reaction equation
[CH2:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:6]2=[N:5][C:4]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:2].[H-].[Na+].[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[C:19]([O:18][C:17]([N:16]([C:4]1[N:5]=[C:6]2[C:11]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:9]=[CH:8][N:7]2[C:3]=1[CH2:1][CH3:2])[S:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:34])=[O:33])=[O:23])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 67966899HCID 67966899, compound

Product 1

HCID 67953998HCID 67953998, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of compound 13-C (0.450 g, 1.37 mmol) in DMF (7.5 mL) at room temperature was added 95% NaH (0.086 g, 3.42 mmol) and the reaction mixture was stirred for 10 minutes. Benzenesulfonyl chloride (0.362 g, 2.05 mmol) dissolved in DMF (2.5 mL) was added and the reaction mixture was stirred at room temperature overnight. The reaction was quenched by the addition of H2O and the solution was extracted with ethyl acetate. After separation of the organic and aqueous layers a sufficient amount of water was added to remove any dissolved DMF from the organic layer. The organic layer was dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure to afford the crude product. The crude material was purified by flash column chromatography, eluting with a hexanes-EtOAc gradient to give compound 13-D (0.552 g, 86%); MS m/z (M+H+) 470.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. customThe reaction was quenched by the addition of H2O
  4. extractionthe solution was extracted with ethyl acetate
  5. customAfter separation of the organic and aqueous layers a sufficient amount of water
  6. additionwas added
  7. customto remove any dissolved DMF from the organic layer
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent evaporated under reduced pressure
  11. customto afford the crude product
  12. customThe crude material was purified by flash column chromatography
  13. washeluting with a hexanes-EtOAc gradient
  14. customto give compound 13-D (0.552 g, 86%)

Sources & evidence

ORD record
ord-cde0596d9d7a49769f0784cf43b77045
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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