HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → 4,4-Difluoro-N-methoxy-N-methylcyclohexanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4,4-Difluorocyclohexanecarboxylic acid | HCID 2779136 | — |
| 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 | 4,4-Difluoro-N-methoxy-N-methylcyclohexanecarboxamide | HCID 58421763 | — |
Reaction Steps
2.78 g HATU were added to a solution of 1 g 4,4-difluoro-cyclohexanecarboxylic acid and 1.3 ml diisopropylethlyamine in 10 ml anhydrous DMF at 0° C. The reaction was stirred at 0° C. for 0.5 hours when 0.891 g O,N-Dimethyl-hydroxylamine hydrochloride were added. The reaction was allowed to warm to rt overnight. The solution was concentrated in vacuo by co-evaporation with toluene (3×) and filtered. The filtrate was concentrated in vacuo. Purification was achieved by silica gel column chromatography (solvent: 5:1→3:1 petroleum ether/EtOAc).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08754079B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-3cb0cbca815b4d70b735c150f5551337 |
| Source note | uspto-grants-2014_06 |