Sodium hydride → HCID 54083775, compound

HRID 429841Notes

Reaction equation

HRID 429841 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][C@@H:18]([N:20]([CH2:23][CH:24]3[CH2:29][CH2:28][N:27]([S:30]([CH:33]=[CH2:34])(=[O:32])=[O:31])[CH2:26][CH2:25]3)[CH2:21][CH3:22])[CH3:19])=[CH:16][C:11]=2[CH2:10][CH2:9]1>CN(C)C=O>[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][C@@H:18]([N:20]([CH2:23][CH:24]3[CH2:29][CH2:28][N:27]([S:30]([CH2:33][CH2:34][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:31])=[O:32])[CH2:26][CH2:25]3)[CH2:21][CH3:22])[CH3:19])=[CH:16][C:11]=2[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 54327231HCID 54327231, compound

Product 1

HCID 54083775HCID 54083775, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of methane sulfonamide (0.18 grams, 1.84 mmole) in dimethylformamide (2 ml) was added 60% sodium hydride (0.048 grams, 1.2 mmole) in mineral oil. The reaction mixture was heated at 120° C. for 30 minutes, and cooled to 100° C. A solution of (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-ethenesulfonylpiperidin-4-ylmethyl)amine (0.36 grams, 0.92 mmol) in dimethylformamide was added all at once. The reaction mixture was heated at 100° C. for 40 minutes. The solvent was evaporated under reduced pressure and the residue was partitioned between dichloromethane and water. The organic layer was dried over potassium carbonate and evaporated to leave a residue, which was purified by flash chromatography using ethyl acetate. Appropriate fractions were combined and evaporated to give (S)-N-{2-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidine-1-sulfonyl]ethyl}-methanesulfonamide as an oil (0.32 grams, 71%). M+H 488. Analysis % of the hydrochloride salt: Found: C, 48.26; H, 7.09; N, 8.10. Requires: C, 48.59; H, 7.42; N, 7.73.

Workup

  1. temperaturecooled to 100° C
  2. temperatureThe reaction mixture was heated at 100° C. for 40 minutes
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between dichloromethane and water
  5. dry with materialThe organic layer was dried over potassium carbonate
  6. customevaporated
  7. customto leave a residue, which
  8. customwas purified by flash chromatography
  9. customevaporated

Sources & evidence

ORD record
ord-d9831bc90f384215958446ddac91926c
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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