Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2,6-Dimethoxypyridin-3-amine | HCID 593005 | — |
| Reactant | 4-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline | HCID 21890421 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 22667085 | HCID 22667085 | 79.7% |
Reaction Steps
4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethyl-aniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (92 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 3-amino-2,6-dimethoxypyridine (70 mg) was added to the reaction solution, and the mixture was stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in a minor amount of chloroform, and a large amount of ether was added to the solution to precipitate a crystal which was then collected by filtration to give 124 mg (yield 79%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06797823B1 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-fdbf69c55c5648d2ac632f74aeebc8a1 |
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| Source note | uspto-grants-2004_09 |
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