HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 131735943, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | HCID 53401839 | HCID 53401839 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 131735943 | HCID 131735943 | 60.5% |
Reaction Steps
3-(6-Bromo-pyridin-2-yl)-acrylic acid (4.5 g, 19.5 mmol) prepared in Step 1, N,O-dimethylhydroxylamine hydrochloride (2.3 g, 23.4 mmol), HOBT (5.3 g, 39.1 mmol), EDAC (7.5 g, 39.1 mmol) and triethylamine (5.4 mL, 39.1 mmol) were added to dichloromethane (100.0 mL). The reaction mixture was stirred at room temperature for 18 hours, quenched with a saturated solution of ammonium chloride, and then extracted with dichloromethane. The extract was washed with 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=1/9) to give 3.2 g of the titled compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376420B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-f25f5dd0aeb54deeb361c6f217e53da5 |
| Source note | uspto-grants-2016_06 |