HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (+/-)-3-Pyridin-2-yl-N-[1-(3-trifluoromethoxyphenyl)ethyl]acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(2-Pyridyl)acrylic acid | HCID 247824 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-[3-(Trifluoromethoxy)phenyl]ethan-1-amine | HCID 22605542 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (+/-)-3-Pyridin-2-yl-N-[1-(3-trifluoromethoxyphenyl)ethyl]acrylamide | HCID 69919610 | — |
Reaction Steps
To a solution of 3-(pyridin-2-yl)acrylic acid, Preparation 16 (50 mg) in CH2Cl2 (2 mL) at room temperature were added (±)-1-(3-trifluoromethoxy phenyl)ethylamine, Preparation 15 (76 mg), EDC hydrochloride (129 mg), DMAP (41 mg), and triethylamine (0.2 mL), and the resulting solution was stirred at room temperature for 12 hours. The crude product was purified by silica gel chromatography eluting with ethyl acetate to provide the title compound as the racemate (96 mg). This racemate was separated by HPLC using AD column eluting with hexanes/ethanol (9:1) to give the title compound as an enantiomer of undetermined chirality.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06831080B2 |
| Source dataset | uspto-grants-2004_12 |
| ORD ID | ord-ab90da8c41264b2190e2bd26b776faf4 |
| Source note | uspto-grants-2004_12 |