Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 22267270 | HCID 22267270 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22267231 | HCID 22267231 | 48% |
Reaction Steps
A solution of 2-[6-[(methylamino)methyl]-7-chloro-2-oxo-4-phenyl-2H-chromen-3-yl]-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide (Example 180)(0.20 g) in THF (5 ml) was combined with triethylamine (0.11 ml) and acetyl chloride (0.033 ml), and stirred for 3 hours. The reaction solution was combined with water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate followed by a saturated brine, and then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue was purified by column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:4), and further recrystallized from ethyl acetate-diisopropyl ether to obtain the title compound as a colorless crystal (105 mg, 48%). Melting point: 199-201° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06974806B2 |
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| Source dataset | uspto-grants-2005_12 |
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| ORD ID | ord-7c4b1c9c77434934b3eea2f6ea3d70c2 |
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| Source note | uspto-grants-2005_12 |
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