HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Pyrazinecarboxylic acid → Methyl 2-(bis-(tert-butoxycarbonyl)amino)-3-(pyrazine-2-carboxamido)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Pyrazinecarboxylic acid | HCID 1047 | — |
| 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 | Methyl 3-amino-2-(bis(tert-butoxycarbonyl)amino)benzoate | HCID 58552839 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 2-(bis-(tert-butoxycarbonyl)amino)-3-(pyrazine-2-carboxamido)benzoate | HCID 58552825 | 58.4% |
Reaction Steps
A solution of methyl 3-amino-2-(bis(tert-butoxycarbonyl)amino)benzoate 13 (3.8 g, 10.4 mmol), pyrazine-2-carboxylic acid 10 (1.54 g, 12.5 mmol), HATU (7.9 g, 20.8 mmol) and DIPEA (2.68 g, 20.8 mmol) in DMF was heated at 50° C. for 12 h. The reaction mixture was poured into H2O and the resulting precipitate was collected by filtration and dried under vacuum. The crude residue was purified by flash chromatography to give 14 (2.87 g, 58% yield)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09326986B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-75f2ef6ebe1d4488bc688f9e05dbe96f |
| Source note | uspto-grants-2016_05 |