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

HRID 574859Notes

Reaction equation

HRID 574859 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-5c127af21a094f02b9b524bcbdc6bba2
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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