HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 178456928, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Bromomethyl)naphthalene-1-carbonitrile | HCID 12433008 | — |
| Reactant | HCID 178456897 | HCID 178456897 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178456928 | HCID 178456928 | 52.1% |
Reaction Steps
To a solution of (5Z)-5-(piperidin-4-ylmethylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) in DMF (3 mL) were added potassium carbonate (345 mg) and 4-(bromomethyl)naphthalene-1-carbonitrile (153 mg). The reaction mixture was stirred at room temperature overnight, water was added, and the mixture was extracted with ethyl is acetate. The extract was washed with water and 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 (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (134 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08772277B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-4463249b2b844b25ac8aa8998ac6c589 |
| Source note | uspto-grants-2014_07 |