Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | Propargylamine | HCID 239041 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline | HCID 11301470 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 22667128 | HCID 22667128 | 87% |
Reaction Steps
4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (150 mg) was dissolved in chloroform (10 ml) and triethylamine (2 ml), and a solution of triphosgene (156 mg) in dichloromethane was added to the solution. The mixture was heated under reflux for 10 min. Next, propargylamine (53 mg) was added, and the mixture was heated under reflux for additional 30 min. 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 anhydrous sodium sulfate. 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 164 mg (yield 87%) 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-95aabed695194a168eb59da5057e06b0 |
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| Source note | uspto-grants-2007_01 |
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