Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allylamine | HCID 7853 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline | HCID 11301470 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 69353451 | HCID 69353451 | 98.9% |
Reaction Steps
4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (100 mg) was dissolved in toluene (5 ml) and triethylamine (1 ml), and a solution of triphosgene (104 mg) in dichloromethane was then added to the solution. The mixture was heated under reflux for 5 min. Next, allylamine (22 mg) was added to the reaction solution, and the mixture was heated under reflux for additional 4 hr. A saturated aqueous sodium hydrogencarbonate solution (1 ml) and chloroform (2 ml) were added to the reaction solution, and the mixture was supported on diatomaceous earth, followed by extraction with chloroform. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1) to give 125 mg (yield 98%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07169789B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-377a42c512014817ae08822d7c33e4a5 |
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| Source note | uspto-grants-2007_01 |
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