Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Fluoro-3-(trifluoromethyl)benzonitrile | HCID 144255 | — |
| Reactant | HCID 178482469 | HCID 178482469 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 178482468 | HCID 178482468 | 11% |
Reaction Steps
To a solution of (5Z)-4-(methylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (100 mg) in dimethyl sulfoxide (2 mL) were added cesium carbonate (327 mg) and 4-fluoro-3-(trifluoromethyl)benzonitrile (76 mg), and the mixture was stirred at 100° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) to give the title compound (14.5 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772277B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-13665c12d87c4a29a3a2cf50e298fb12 |
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| Source note | uspto-grants-2014_07 |
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