Sodium hydride → N-(6-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]pyrid-3-yl}-N-methylmethanesulphonamide

HRID 256610Notes

Reaction equation

HRID 256610 reaction equation
[H-].[Na+].Cl[C:4]1[N:9]=[CH:8][C:7]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[SH:16][C:17]1[CH:18]=[C:19]([C:23]2([O:29][CH3:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1>CN(C=O)C>[CH3:30][O:29][C:23]1([C:19]2[CH:18]=[C:17]([S:16][C:4]3[N:9]=[CH:8][C:7]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 193757154-(3-Mercaptophenyl)-4-methoxytetrahydropyranHCID 19785594N-(6-chloropyrid-3-yl)-N-methylmethanesulphonamide

Product 1

HCID 19743039N-(6-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]pyrid-3-yl}-N-methylmethanesulphonamideYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (79 mg, 50% dispersion in mineral oil, 1.65 mmol) was added to a solution of N-(6-chloropyrid-3-yl)-N-methyl-methanesulphonamide (0.33 g) and 4-(3-mercaptophenyl)-4-methoxytetrahydropyran (0.34 g) in DMF (10 ml). The mixture was stirred at ambient temperature for 15 minutes and heated at 140° C. for 1.5 hours. After cooling, it was partitioned between water (75 ml) and ethyl acetate (75 ml). The organic phase was washed with brine (50 ml), dried (MgSO4) and the solvent evaporated. The product was purified by column chromatography to give N-(6-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]pyrid-3-yl}-N-methylmethanesulphonamide as a gum (0.25 g, 41%).

Workup

  1. temperatureheated at 140° C. for 1.5 hours
  2. temperatureAfter cooling
  3. customit was partitioned between water (75 ml) and ethyl acetate (75 ml)
  4. washThe organic phase was washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-6594e3b162894be181d48e52cb146b5a
Source dataset
uspto-grants-1993_11
Patent number
US05258399

Reaction notes

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