HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylacetamide → Alvelestat
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 6-Methyl-5-(1-methyl-1H-pyrazol-5-yl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid | HCID 59455875 | — |
| Reactant | [5-(Methanesulfonyl)pyridin-2-yl]methanaminium chloride | HCID 66725223 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Alvelestat | HCID 46861623 | 20.4% |
Reaction Steps
HBTU (30 mg, 0.079 mmol) was added to {[5-(methylsulfonyl)pyridin-2-yl]methyl}amine hydrochloride (20 mg, 0.090 mmol), 6-methyl-5-(2-methyl-2H-pyrazol-3-yl)-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid (Example 92 (a), 27 mg, 0.072 mmol) and DMA (23 μl, 0.31 mmol) in NMP (0.25 ml) and the mixture was stirred in a sealed vial overnight. The product was purified by preparative HPLC and freeze-dried to give the title compound as a white solid (8 mg, 20%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08501784B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-8ae898f73f294ced88c8b6e90956db7e |
| Source note | uspto-grants-2013_08 |