HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1-((5-Cyanopyridin-2-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | (3-Trifluoromethylphenyl)urea | HCID 25712 | — |
| Reactant | 6-Formylpyridine-3-carbonitrile | HCID 21364144 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-((5-Cyanopyridin-2-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea | HCID 86732317 | — |
Reaction Steps
Trimethylsilyl chloride (125 μL, 0.98 mmol) is added to a solution of cyclohexane-1,3-s dione (100 mg, 0.89 mmol), 6-formylnicotinonitrile (118 mg, 0.89 mmol) and 1-(3-(trifluoromethyl)phenyl)urea (182 mg, 0.89 mmol) in a mixture of N,N-dimethyl-formamide (670 μL) and acetonitrile (1.2 mL), and the mixture is stirred at room temperature for 1.5 h. The reaction mixture is cooled to room temperature and poured into a mixture of water and ice. The mixture is filtered, and the precipitate is washed with water and dried under reduced pressure. Yield: 330 mg; ESI mass spectrum [M+H]+=431, Retention time HPLC: 0.63 min (V011_S01).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115093B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-98cd3d6ef57146939d054ecc601125f6 |
| Source note | uspto-grants-2015_08 |