HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,5-Dichloro-nicotinoyl chloride | HCID 2799996 | — |
| Reactant | 1-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one | HCID 58168367 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Solvent | Water ethylacetate | HCID 22728543 | — |
| Product | 2,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide | HCID 58168327 | 64.5% |
Reaction Steps
Compound 137 (40 mg, 0.13 mmol), 2,5-dichloro-nicotinoyl chloride (28 mg, 0.13 mmol), and DIEA (0.02 mL, 0.13 mmol) were suspended in dioxane (2 mL), and stirred overnight at room temperature. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 180 (40 mg, 64% yield) as a white solid. LC-MS (M+H=478, obsd.=478).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08735584B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-6086b94094634432a2e6dc0c1eea5f42 |
| Source note | uspto-grants-2014_05 |