HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Aminoquinoline → 1-((2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-3-yl)urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Aminoquinoline | HCID 11375 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | (2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine | HCID 58873687 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-((2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-3-yl)urea | HCID 71237213 | 42% |
Reaction Steps
1,1′-Carbonyldiimidazole (CU) (1.1 eq.) was added to 3-aminoquinoline (1 eq.) dissolved in methylene chloride. The mixture was stirred during 12 h at room temperature. After that (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (0.98 eq.) was added to the mixture. After 12 h the solvent was evaporated and the mixture was purified by column chromatography (silica gel: 100-200; eluent: 50% ethyl acetate in n-hexane) and give the desired 1-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-3-yl)urea (example compound 12) (100 mg, 42%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029378B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-a7d0454ff2be44b3a731740fc35597db |
| Source note | uspto-grants-2015_05 |