HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 8-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid (3-pyridin-4-yl-phenyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-(4-Pyridyl)aniline | HCID 459523 | — |
| Reactant | 8-Hydroxy-3-carboxy-coumarin | HCID 7245716 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 8-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid (3-pyridin-4-yl-phenyl)-amide | HCID 44123667 | 42.1% |
Reaction Steps
DIEA (0.028 mL, 0.160 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.030 g, 0.146 mmol) and HATU (0.061 g, 0.160 mmol) in 0.5 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-pyridin-4-ylaniline (0.025 g, 0.146 mmol) was added and allowed to react overnight when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 0.022 g of product in 42% yield: LCMS (ESI) m/z 359 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642788B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-733f4b63692149afa540a2d03d0efe53 |
| Source note | uspto-grants-2014_02 |