Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Sodium Bicarbonate | HCID 516892 | — |
| Edukt | 4-Chloro-2-(trifluoromethyl)benzaldehyde | HCID 2779017 | — |
| Edukt | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Edukt | HCID 178459303 | HCID 178459303 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Triethylamine | HCID 8471 | — |
| Produkt | HCID 178459307 | HCID 178459307 | 30,7% |
Reaktionsschritte
To a solution of (5Z)-4-[(2-hydroxy-2-methylpropyl)amino]-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) in DMF (2 mL) was added a solution of triethylamine (0.32 mL) and 4-chloro-2-(trifluoromethyl)benzaldehyde (117 mg) in DMF (1 mL). The reaction mixture was stirred at room temperature for 1 hr, and sodium triacetoxyborohydride (501 mg) was added. The reaction mixture was stirred at room temperature overnight, 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 (82 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-7108e499e25045ada9f9500c4e86e907 |
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| Quellennotiz | uspto-grants-2014_07 |
|---|