HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → HCID 24812093, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Amino-4-picoline | HCID 137935 | — |
| Reactant | PMID26882240-Compound-8 | HCID 625381 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 24812093 | HCID 24812093 | 51.6% |
Reaction Steps
To solution of (4-adamantan-1-yl-phenoxy)-acetic acid (50 mg, 0.17 mmol), 5-amino-4-picoline (28.32 mg, 0.26 mmol) and DIPEA (33.85 mg, 0.26 mmol) in DMF 1 mL was added EDC (50.2 mg, 0.26 mmol) and HOBt (35.39 mg, 0.26 mmol) at room temperature. Reaction mixture was stirred at room temperature. Resulting mixture poured onto ice cold water, was extracted with ethyl acetate, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜2:8) to give 2-(4-adamantan-1-yl-phenoxy)-N-(4-methyl-pyridine-2-yl)-acetamide as a colorless solid (0.033 g, 50% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394799B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-0d170a191e584879816e80886eb03c51 |
| Source note | uspto-grants-2013_03 |