HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(3-methylbenzo[b]thiophen-2-ylmethyl)acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid | HCID 10487224 | — |
| Reactant | N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamine | HCID 22593745 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(3-methylbenzo[b]thiophen-2-ylmethyl)acrylamide | HCID 22593722 | 72.2% |
Reaction Steps
To a stirred solution of 3-methyl-2-(methylaminomethyl)benzo[b]thiophene (0.30 g, 1.6 mmole) in 1:1 DMF/CH2Cl2 was added (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.33 g, 2 mmole), HOBt.H2O (0.27 g, 2 mmole), and DCC (0.41 g, 2 mmole). The reaction was stirred for 16 hr, then was concentrated under vacuum. The residue was taken up in CHCl3, washed with H2O, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (4% methanol/CHCl3) gave the title compound (0.39 g, 72%) as a pale yellow solid: LCMS (ES) m/e 338.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173646B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-fdbda2a1a43d4a23b573f7dad33380f5 |
| Source note | uspto-grants-2012_05 |