Tetrahydrofuran → HCID 23114775, compound

HRID 2080505Notes

Reaction equation

HRID 2080505 reaction equation
O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:24][C:25]1[C:26]([CH:40]([C:52]2[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:53]=2[F:59])[S:41]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[C:46]([F:51])[CH:45]=2)(=[O:43])=[O:42])=[CH:27][C:28]([N:31](S(C)(=O)=O)[S:32]([CH3:35])(=[O:34])=[O:33])=[N:29][CH:30]=1.CCCCCC>C(OCC)(=O)C>[Cl:24][C:25]1[C:26]([CH:40]([C:52]2[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:53]=2[F:59])[S:41]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[C:46]([F:51])[CH:45]=2)(=[O:43])=[O:42])=[CH:27][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 2724141Tetrabutylammonium FluorideHCID 23114788HCID 23114788, compound

Product 1

HCID 23114775HCID 23114775, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, a tetrahydrofuran solution (1M, 0.147 ml, 0.15 mmol) of tetrabutylammonium fluoride was added to a tetrahydrofuran (2 ml) solution of N-[5-chloro-4-[(2,5-difluorophenyl)(3,4-difluorophenylsulfonyl)methyl]pyridin-2-yl]-N-(methylsulfonyl)methanesulfonamide (72 mg, 0.12 mmol). The resulting mixture was stirred at room temperature for 2 hours. After the reaction mixture was concentrated under reduced pressure, the residue thus obtained was dissolved in ethyl acetate. The resulting solution was washed sequentially with 1N hydrochloric acid and a saturated aqueous solution of ammonium chloride. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure. The residue thus obtained was washed with a mixed solvent of diethyl ether/hexane and collected by filtration to give the title compound (53 mg, 0.10 mmol, 84%) as a white solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washThe resulting solution was washed sequentially with 1N hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure
  9. customThe residue thus obtained
  10. washwas washed with a mixed solvent of diethyl ether/hexane
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c8b14bd6e2e04dde8b59b5ed52705089
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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