Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(Trifluoromethyl)benzoyl chloride | HCID 67561 | — |
| Reactant | 2-amino-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloxime | HCID 118071603 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 118071566 | HCID 118071566 | 69.5% |
Reaction Steps
To a solution of 227 mg of 2-amino-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloxime and 92 mg of triethylamine in 5 ml of dichloromethane, 175 mg of 2-(trifluoromethyl)benzoyl chloride was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 1 hour. After completion of the reaction, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (10 ml×1), the resulting organic layer was washed with water (10 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 249 mg of the desired product as a colorless resinous substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09434684B2 |
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| Source dataset | uspto-grants-2016_09 |
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| ORD ID | ord-59e720b8f02341e79c795e1ea4824d2e |
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| Source note | uspto-grants-2016_09 |
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