Water → N-{5-bromo-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-N-methylmethanesulfonamide

HRID 2411354Notes

Reaction equation

HRID 2411354 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][N:22]=3)[CH2:17][CH2:16]2)=[O:14])=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.[H-].[Na+].[CH3:31]I.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([N:15]2[CH2:16][CH2:17][N:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][N:22]=3)[CH2:19][CH2:20]2)=[O:14])=[C:6]([N:8]([CH3:31])[S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58484868N-{5-bromo-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}methanesulfonamide

Product 1

HCID 71252240N-{5-bromo-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{5-bromo-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}methanesulfonamide (634 mg) described in Preparation Example 226 was dissolved in N,N-dimethylformamide (5 mL), and sodium hydride (65.1 mg, 60% in oil) was added under ice-cooling. After stirring at room temperature for 10 min, methyl iodide (93 μL) was added, and the mixture was stirred overnight. To the reaction mixture was added water under ice-cooling, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (670 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-c7ffe3f1519145c18cbb1de19f06dd83
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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