Dimethyl Sulfoxide → HCID 66817982, compound

HRID 1755053Notes

Reaction equation

HRID 1755053 reaction equation
CS(C)=[O:3].[OH-].[Na+].OO.[NH2:9][C:10]1([C:31]#[N:32])[CH2:15][CH2:14][N:13]([S:16](/[CH:19]=[CH:20]/[C:21]2[C:26]([CH3:27])=[CH:25][C:24]([NH:28][CH3:29])=[CH:23][C:22]=2[CH3:30])(=[O:18])=[O:17])[CH2:12][CH2:11]1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CO>[NH2:9][C:10]1([C:31]([NH2:32])=[O:3])[CH2:15][CH2:14][N:13]([S:16](/[CH:19]=[CH:20]/[C:21]2[C:22]([CH3:30])=[CH:23][C:24]([NH:28][CH3:29])=[CH:25][C:26]=2[CH3:27])(=[O:17])=[O:18])[CH2:12][CH2:11]1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 66817117HCID 66817117, compound

Product 1

HCID 66817982HCID 66817982, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

DMSO (0.9 ml, 12.8 mmol), a 1 N aqueous NaOH solution (1.06 ml, 1.06 mmol) and 30% aqueous hydrogen peroxide (0.72 ml, 6.40 mmol) were sequentially added to a solution of 4-amino-1-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-piperidine-4-carbonitrile (1.85 g, 5.33 mmol) in MeOH (30 ml) at 0° C., and the mixture was stirred at room temperature for 2.5 hours. A saturated Na2S2O3 solution was added to the reaction mixture, and the precipitated solid was obtained by suction filtration. The resulting solid was washed with water, dissolved in a CH2Cl2-MeOH (3:2) solution, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was triturated with hexane:CH2Cl2=4:1 to give 4-amino-1-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-piperidine-4-carboxylic amide (1.36 g, 70%).

Workup

  1. customthe precipitated solid was obtained by suction filtration
  2. washThe resulting solid was washed with water
  3. dissolutiondissolved in a CH2Cl2-MeOH (3:2) solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-4ec412524a4447c2830987deec039bf5
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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