HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilyl cyanide → (3-Methoxy-5-methoxymethylphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilyl cyanide | HCID 82115 | — |
| Reactant | Ytterbium triflate | HCID 2733225 | — |
| Reactant | 4-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline | HCID 18188176 | — |
| Reactant | 2-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid Trifluoroacetate | HCID 136337083 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3-Methoxy-5-methoxymethylphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile | HCID 59516906 | — |
Reaction Steps
To a solution of the residue in 10 ml of dichloromethane there was added 550 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 1g of MS3A, 195 mg of Yb(OTf)3 and 0.79 ml of trimethylsilyl cyanide, and the mixture was stirred at room temperature for 20 hours under a nitrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.25 g) as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07928228B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-040e670c1e9f4341b342a22daa81d55a |
| Source note | uspto-grants-2011_04 |