HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylacetamide → 6-Methyl-5-(2-methyl-2H-pyrazol-3-yl)-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid cyanomethyl amide
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 | Aminoacetonitrile hydrochloride | HCID 11491918 | — |
| Reactant | 6-Methyl-5-(1-methyl-1H-pyrazol-5-yl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid | HCID 59455875 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 6-Methyl-5-(2-methyl-2H-pyrazol-3-yl)-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid cyanomethyl amide | HCID 86614785 | 72.2% |
Reaction Steps
The compound obtained in step (a) (0.2 g, 0.53 mmol) was dissolved in 1,4-dioxane (5 ml), HBTU (0.19 g, 0.5 mmol) and DMA (0.32 g, 2.5 mmol). The mixture was stirred for 10 minutes and aminoacetonitrile hydrochloride (0.55 g, 0.6 mmol) was added. After 1 h the mixture was evaporated and the residue purified by chromatography on silica to give the amide (0.15 g, 72%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08501784B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-a6985feec92942708ff1f7964f8657f4 |
| Source note | uspto-grants-2013_08 |