HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-N-(1-benzyl-1H-indol-3-ylmethyl)-N-methylacrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-benzyl-3-(methylaminomethyl)-1H-indole | HCID 12283876 | — |
| Reactant | 3-(6-Aminopyridin-3-yl)prop-2-enoic acid | HCID 53400832 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (E)-3-(6-aminopyridin-3-yl)-N-(1-benzyl-1H-indol-3-ylmethyl)-N-methylacrylamide | HCID 9930640 | 60.5% |
Reaction Steps
EDC (0.42 g, 2.20 mmole) was added to a solution of 3-(6-aminopyridin-3-yl)acrylic acid (0.36 g, 2.20 mmole), 1-benzyl-3-(methylaminomethyl)-1H-indole (0.50 g, 2.00 mmole), HOBt.H2O (0.30 g, 22.0 mmole) and diisopropylethylamine (0.70 mL, 4.00 mmole) in DMF (30 mL) at RT. The reaction was stirred overnight, then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (10% MeOH/CHCl3) gave the title compound (0.48 g, 60%) as a light yellow solid: MS (ES) m/e 397 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173646B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-82508336373243e3a03044b57f7f62b6 |
| Source note | uspto-grants-2012_05 |