HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid [4-(1H-benzoimidazol-2-yl)-phenyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid | HCID 234562 | — |
| Reactant | 4-(1H-1,3-benzodiazol-2-yl)aniline | HCID 345677 | — |
| 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-Methoxy-2-oxo-2H-chromene-3-carboxylic acid [4-(1H-benzoimidazol-2-yl)-phenyl]-amide | HCID 86650471 | 75% |
Reaction Steps
DIEA (43.5 μL, 0.25 mmol) was added to 8-methoxy-3-carboxy-coumarin (50.0 mg, 0.23 mmol) and HATU (95.0 mg, 0.25 mmol) in 1 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 4-(1H-benzoimidazol-2-yl)-phenylamine (47.5 mg, 0.23 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 71.0 mg of product in 75% yield: LCMS (ESI) m/z 412 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642788B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-a842ea7220e44d12a849aef82e8c5479 |
| Source note | uspto-grants-2014_02 |