HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-[(1-Methyl-1-{1-[2-(methylsulfonyl)-4-(trifluoromethoxy)benzoyl]piperidin-4-yl}ethyl)sulfonyl]-6-(trifluoromethyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 2-(Methylsulfonyl)-4-(trifluoromethoxy)benzoic acid | HCID 59447309 | — |
| Reactant | 2-[(1-Methyl-1-piperidin-4-ylethyl)sulfonyl]-6-(trifluoromethyl)pyridine | HCID 59447431 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | 2-[(1-Methyl-1-{1-[2-(methylsulfonyl)-4-(trifluoromethoxy)benzoyl]piperidin-4-yl}ethyl)sulfonyl]-6-(trifluoromethyl)pyridine | HCID 59447181 | — |
Reaction Steps
To a 10 ml vial was added 2-(methylsulfonyl)-4-(trifluoromethoxy)benzoic acid (16.9 mg, 0.059 mmol), 2-[(1-methyl-1-piperidin-4-ylethyl)sulfonyl]-6-(trifluoromethyl)pyridine (20 mg, 0.059 mmol), Bop reagent (31.6 mg, 0.071 mmol), diisopropylethyl amine (0.052 ml, 0.297 mmol) and 1 ml dimethylformamide. The resulting solution was stirred at room temperature for 1 hour. It was diluted with 1 m dimethyl sulfoxide, 0.5 ml water and 0.1 ml trifluoroacetic acid. This mixture was loaded on to reverse phase column directly and eluted with water acetonitrile gradient solvent to give the title compound as fluffy white solid after lyophilizing.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08304434B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-b8b50378c77a4b3195d3d8de95b36b44 |
| Source note | uspto-grants-2012_11 |