HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → HCID 9818411, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methyl[(naphthalen-2-yl)methyl]amine | HCID 541935 | — |
| Reactant | (2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid | HCID 10487224 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | HCID 9818411 | HCID 9818411 | 85.8% |
Reaction Steps
To a stirred solution of (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.30 g, 1.8 mmole) in 1:1 DMF/CH2Cl2 (25 mL) was added 2-(methylaminomethyl)naphthalene (0.34 g, 2 mmole), HOBt.H2O (0.27 g, 2 mmole), Et3N (0.28 mL, 2 mmole), and EDC (0.38 g, 2 mmole). After stirring at RT for 16 hr the reaction was concentrated under vacuum. The residue was taken up in ethyl acetate and the solution was washed with H2O, dried (Na2SO4) and concentrated to dryness. Purification by flash chromatography on silica gel (4% methanol/CHCl3), trituration with 1:1 ethyl acetate/hexane, filtration, and drying under vacuum gave the title compound (0.49 g, 81%) as an off-white solid: LCMS (ES) m/e 318.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07524843B2 |
| Source dataset | uspto-grants-2009_04 |
| ORD ID | ord-c92cece94d45432fa5c4ed366dfbe76e |
| Source note | uspto-grants-2009_04 |