Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | 1-Naphthaldehyde | HCID 6195 | — |
| Edukt | Sodium Bicarbonate | HCID 516892 | — |
| Edukt | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Edukt | HCID 178456897 | HCID 178456897 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Triethylamine | HCID 8471 | — |
| Produkt | HCID 178456900 | HCID 178456900 | — |
Reaktionsschritte
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 triethylamine (0.35 mL) and naphthalene-1-carbaldehyde (0.09 mL). The reaction mixture was stirred at room temperature for 1 hr, and sodium triacetoxyborohydride (554 mg) was added. The reaction mixture was stirred at room temperature for 3 hr, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl 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 (104 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08772277B2 |
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| Quelldatensatz | uspto-grants-2014_07 |
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| ORD ID | ord-453f5247c66147cb840bcc81ed3e4ba0 |
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| Quellennotiz | uspto-grants-2014_07 |
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