HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Aminopyridine → 5-Acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Aminopyridine | HCID 10009 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 5-Acetyl-2-(benzyloxy)benzoic acid | HCID 21880613 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 5-Acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide | HCID 67107252 | — |
Reaction Steps
Diisopropylethylamine (0.97 ml, 5.55 mmol), 3-aminopyridine (418 mg, 4.44 mmol) and HATU (1.27 g, 3.33 mmol) were added to a solution of 5-acetyl-2-[(phenylmethyl)oxy]benzoic acid (commercially available from Acros; 600 mg, 2.22 mmol) in dimethylformamide (10 ml). The solution was stirred for 2 hours. Ethyl acetate (40 ml) and H2O (40 ml) were added and the organic layer washed with H2O (3×20 ml), dried and the solvent removed in vacuo to give a solid. Trituration with 3:1 hexane/ethyl acetate yielded the title compound as a yellow solid. 541 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08778939B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-5e16427e51254d8c96db2d14f471f0d7 |
| Source note | uspto-grants-2014_07 |