Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 118431833 | HCID 118431833 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 118432072 | HCID 118432072 | 44.9% |
Reaction Steps
1-(2-Chloro-phenyl)-5-[4-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole trifluoroacetate (15.0 mg, 0.02 mmol) prepared in Example 292, triethylamine (9.3 uL, 0.07 mmol) and acetyl chloride (3.6 uL, 0.03 mmol) were added at 0° C. to dichloromethane (1.0 mL). The reaction mixture was stirred at room temperature for 2 hours and then distilled water was added thereto. The reaction mixture was extracted with dichloromethane two times. The combined extract was washed with 1N hydrochloric acid, a saturated solution of sodium carbonate, and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3) to give 4.9 mg of the titled compound as a yellow liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376420B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-d00a0c48c00f470297361d089eec39a5 |
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| Source note | uspto-grants-2016_06 |
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