Potassium Cyanide → HCID 90224811, compound

HRID 1487093Notes

Reaction equation

HRID 1487093 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:21]2[C:25]([CH3:27])([CH3:26])[C:24](=[O:28])[NH:23][C:22]2=[O:29])[CH:5]=[C:6]([CH3:20])[C:7]=1/[CH:8]=[CH:9]/[S:10]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)(=[O:12])=[O:11].[C-:30]#[N:31].[K+].C([O-])(=O)C.[NH4+:37]>CO>[NH2:37][C:16]1([C:30]#[N:31])[CH2:17][CH2:18][N:13]([S:10](/[CH:9]=[CH:8]/[C:7]2[C:6]([CH3:20])=[CH:5][C:4]([N:21]3[C:25]([CH3:26])([CH3:27])[C:24](=[O:28])[NH:23][C:22]3=[O:29])=[CH:3][C:2]=2[CH3:1])(=[O:12])=[O:11])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 517165Ammonium AcetateHCID 90224810HCID 90224810, compound

Product 1

HCID 90224811HCID 90224811, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (E)-1-(3,5-dimethyl-4-(2-((4-oxopiperidin-1-yl)sulfonyl)vinyl)phenyl)-5,5-dimethylimidazolidine-2,4-dione (994 mg, 2.37 mmol) in methanol (24 mL), potassium cyanide (188 mg, 2.84 mmol) and ammonium acetate (237 mg, 3.08 mmol) were added at room temperature. The mixture was stirred at 60-70° C. for three hours. The reaction mixture was cooled, concentrated under reduced pressure, and then diluted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to afford (E)-4-amino-1-((4-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-2,6-dimethylstyryl)sulfonyl)piperidine-4-carbonitrile (681 mg, 68%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-04fdfbbe0a1743c58efc1454827891ff
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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