HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetyl chloride → 5-[3-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-(2-chloro-phenyl)-5-[3-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole trifluoroacetate | HCID 118431903 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-[3-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole | HCID 118431693 | 27.5% |
Reaction Steps
1-(2-Chloro-phenyl)-5-[3-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole trifluoroacetate (11.0 mg, 0.02 mmol) prepared in Example 230, acetyl chloride (1.5 uL, 0.02 mmol), and triethylamine (7.5 uL, 0.05 mmol) were added to dichloromethane (0.5 mL). The reaction mixture was stirred at room temperature for 1 hour, washed with distilled water 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=1/1) to give 3.0 mg of the titled compound as a yellow liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376420B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-0c1008f3be3a4682b1ecc7a2741a5fff |
| Source note | uspto-grants-2016_06 |