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

HRID 2254669Notes

Reaction equation

HRID 2254669 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-methylmethanesulphonamide

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-methylmethanesulphonamide (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-c1adf783f5b2489489897d3b633c7170
Source dataset
uspto-grants-1993_08
Patent number
US05236948

Reaction notes

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