Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Oxalyl chloride | HCID 65578 | — |
| Edukt | 2-Methyl-4-(piperazin-1-yl)quinoline | HCID 702318 | — |
| Edukt | trans-2-Octenoic acid | HCID 5282714 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 56949205 | HCID 56949205 | 77% |
Reaktionsschritte
(E)-Oct-2-enoic acid (71.1 mg, 0.5 mmol) was dissolved in dichloromethane (1 ml) and a 2M solution of oxalyl chloride in dichloromethane was added (0.3 ml, 0.6 mmol). The solution was stirred at room temperature for one hour after which a drop of DMF was added. Stirring was continued for another hour, the mixture was evaporated to dryness under reduced pressure. The residue was dissolved in dichloromethane (1 ml), the resulting solution was added to a solution of 2-methyl-4-piperazin-1-yl-quinoline (103 mg, 0.45 mmol) and triethylamine (90 μl, 0.64 mmol) in dichloromethane (1 ml). The resulting mixture was stirred at room temperature overnight, diluted with dichloromethane (1 ml), washed with water and 2M NaOH (2 ml each) and evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 121.3 mg of a solid (0.34 mmol, 77%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08883791B2 |
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| Quelldatensatz | uspto-grants-2014_11 |
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| ORD ID | ord-1305db22f8584012a435e8e4486283d0 |
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| Quellennotiz | uspto-grants-2014_11 |
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