Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 2-Amino-5-bromopyridine | HCID 70622 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline | HCID 21890439 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 22667226 | HCID 22667226 | 41.3% |
Reaction Steps
4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethyl-aniline (120 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (110 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 2-amino-5-bromopyridine (192 mg) was added to the reaction solution, and the mixture was stirred at room temperature for 2 hr. Methanol was added to the reaction solution, and the solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol (91/9). The solvent was removed by distillation, and a crystal was precipitated from a minor amount of methanol and a large amount of ether. The crystal was collected by filtration to give 80 mg (yield 41%) 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-def486fcba23495699935867aecd9712 |
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| Source note | uspto-grants-2004_09 |
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