HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-{[2-([Ethylsulfanyl]methyl)-1-(2-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxypropyl]amino}-1H-quinolin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethanethiol | HCID 6343 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-{[(2-Fluoro-4-methoxyphenyl)(2-trifluoromethyl-oxiranyl)methyl]amino}-1H-quinolin-2-one | HCID 86630555 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-{[2-([Ethylsulfanyl]methyl)-1-(2-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxypropyl]amino}-1H-quinolin-2-one | HCID 42623188 | 35.4% |
Reaction Steps
To 50 mg (0.12 mmol) 5-{[(2-Fluoro-4-methoxyphenyl)(2-trifluoromethyl-oxiranyl)methyl]amino}-1H-quinolin-2-one and 80 mg Cs2CO3 in 0.5 ml DMF are added 14 μl (0.18 mmol) of ethyl mercaptan in DMF. The mixture is stirred vigorously for 4 hours and water is added. The aqueous layer is extracted with ethyl acetate, the organic phases washed with brine and dried over sodium sulphate. After removal of the solvent thin layer chromatography on silica gel (acetone in hexane 50%) yields 20 mg of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394958B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-425b8c4f5ba34736be839f04fae6aa77 |
| Source note | uspto-grants-2013_03 |