Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | HCID 90224810 | HCID 90224810 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 90224811 | HCID 90224811 | 68% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428505B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-04fdfbbe0a1743c58efc1454827891ff |
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| Source note | uspto-grants-2016_08 |
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