HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxalyl chloride → HCID 71765322, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4,4,4-Trifluorocrotonic acid | HCID 5709614 | — |
| Reactant | HCID 20785294 | HCID 20785294 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71765322 | HCID 71765322 | 54% |
Reaction Steps
(E)-4,4,4-Trifluorobut-2-enoic acid (34 mg, 0.24 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (21 μl, 0.24 mmol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 10 minutes. This solution was added to a solution of 1-(2-piperazin-1-yl-4-pyridyl)ethanone (41 mg, 0.2 mmol) and DIPEA (105 μl, 0.6 mmol) in anhydrous DCM (2 ml) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 37 mg of a solid (0.108 mmol, yield 47%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09260441B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-f9315279fdf04a5d858c14e3c548f3ee |
| Source note | uspto-grants-2016_02 |