HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-Fluoro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-ylamino)-phenyl]-2-trifluoromethyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | N-(4-Aminophenyl)-4-fluoro-2-trifluoromethyl-benzamide | HCID 44603462 | — |
| Reactant | 1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one | HCID 58168008 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 4-Fluoro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-ylamino)-phenyl]-2-trifluoromethyl-benzamide | HCID 58167984 | 73% |
Reaction Steps
To a suspension of 83 (135 mg, 0.59 mmol) in ether (10 mL) was added HCl (1.17 mL, 1.00 M, 1.17 mmol) in ether. The mixture was stirred for 3 h and the solvent was removed under vacuo. A suspension of this HCl salt in NMP (3 mL) was added N-(4-aminophenyl)-4-fluoro-2-(trifluoromethyl)benzamide (209 mg, 0.70 mmol). The mixture was stirred at 150° C. for 3 h. After cooling to room temperature, H2O was added. The resulting product precipitate and the solid was filtered, washed with H2O and MeOH, and dried under vacuum to provide 378 (210 mg, 73% yield) as pale solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08735584B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-152b052780c44224ad1834c463c05dd5 |
| Source note | uspto-grants-2014_05 |