HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,2-Dichloroethane → (E)-N-[1-(2-hydroxyethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 1,2-Dichloroethane | HCID 11 | — |
| Edukt | Water | HCID 962 | — |
| Edukt | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 1-ethyl-3-(methylaminomethyl)-1H-indole | HCID 22139101 | — |
| Edukt | (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride | HCID 66905305 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | (E)-N-[1-(2-hydroxyethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide | HCID 66780748 | 61% |
Reaktionsschritte
EDC (0.35 g, 1.81 mmole) was added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride salt (0.42 g, 1.65 mmole), 1-ethyl-3-(methylaminomethyl)-1H-indole (0.31 g, 1.65 mmole), HOBt.H2O (0.24 g., 1.81 mmole) and diisopropylethylamine (0.86 mL, 4.95 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (10% EtOH/EtOAc) gave title compound (0.39 g, 61%) as a light yellow solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07250424B2 |
| Quelldatensatz | uspto-grants-2007_07 |
| ORD ID | ord-679fbe2697d04cedbd378a8e4a45d52b |
| Quellennotiz | uspto-grants-2007_07 |