HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-(5-bromo-2-(piperidin-1-yl)pyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 4-Chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline | HCID 59631025 | — |
| Reactant | 5-Bromo-2-(piperidin-1-yl)pyridin-3-amine | HCID 59631488 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | N-(5-bromo-2-(piperidin-1-yl)pyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine | HCID 59631584 | — |
Reaction Steps
5-Bromo-2-(piperidin-1-yl)pyridin-3-amine (0.0537 g, 0.210 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.0632 g, 0.217 mmol), and hydrochloric acid, 4.0M in 1,4-dioxane (0.05 mL, 0.200 mmol) were stirred in NMP (0.50 mL) then microwaved at 150° C. After an additional 4 h, the reaction was diluted with EtOAc and washed once with satd aq. sodium bicarbonate and once with brine. After drying over anhydrous sodium sulfate, filtration, and concentration, the brown residue was purified with silica gel chromatography (0-40% EtOAc in hexanes) to yield mostly N-(5-bromo-2-(piperidin-1-yl)pyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. Mass Spectrum (ESI) m/e=510.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08940724B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-fef35be93ed14a2d85cce855da625536 |
| Source note | uspto-grants-2015_01 |