Hydrochloric Acid → 4-((4-Fluorotetrahydro-2h-pyran-4-yl)methoxy)-3-(trifluoromethylsulfonyl)benzenesulfonamide

HRID 2040218Notes

Reaction equation

HRID 2040218 reaction equation
[F:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][C:14]=1[S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24].Cl>O1CCCC1.ClCCl>[F:1][C:2]1([CH2:8][O:9][C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][C:14]=2[S:23]([C:26]([F:27])([F:29])[F:28])(=[O:25])=[O:24])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 250584524-Fluoro-3-((trifluoromethyl)sulfonyl)benzenesulfonamideHCID 56971676(4-Fluorooxan-4-yl)methanol

Product 1

HCID 671265454-((4-Fluorotetrahydro-2h-pyran-4-yl)methoxy)-3-(trifluoromethylsulfonyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of EXAMPLE 37C (0.500 g) in tetrahydrofuran (5 mL) was added sodium hydride (0.596 g). Additional tetrahydrofuran (25 mL) was added and the mixture stirred for 30 minutes, then 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide (1.145 g) was added as a solution in tetrahydrofuran (5 mL). After stirring for 2 hours, the reaction mixture was partioned between 1N aqueous HCl (50 mL) and dichloromethane (200 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The resulting solid was chromatographed over silica gel (Reveleris 80 g) eluting with a gradient of 0.5% to 7.5% methanol/dichloromethane over 30 minutes (flow=40 mL/min) to provide the title compound.

Workup

  1. stirringAfter stirring for 2 hours
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was chromatographed over silica gel (Reveleris 80 g)
  6. washeluting with a gradient of 0.5% to 7.5% methanol/dichloromethane over 30 minutes (flow=40 mL/min)

Sources & evidence

ORD record
ord-1b22f4c7cdf947dd9f571465657cbbc3
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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