HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid → N-(2-Methanesulfonyl-ethyl)-N-(4-o-tolyl-pyridin-3-yl)-2,6-bis-trifluoromethyl-isonicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid | HCID 30689135 | — |
| Reactant | (2-Methanesulfonyl-ethyl)-(4-o-tolyl-pyridin-3-yl)-amine | HCID 70663340 | — |
| Product | N-(2-Methanesulfonyl-ethyl)-N-(4-o-tolyl-pyridin-3-yl)-2,6-bis-trifluoromethyl-isonicotinamide | HCID 86670776 | 10% |
Reaction Steps
The title compound was prepared in analogy to example 90, from (2-methanesulfonyl-ethyl)-(4-o-tolyl-pyridin-3-yl)-amine and 2,6-bis(trifluoromethyl)isonicotinic acid (Key Organics Ltd.) after a reaction time of 17 hours. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). A second chromatography (preparative HPLC (phenomenex gemini column), gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2)) yielded the desired product as an off-white solid (10%). MS (ESI): m/z=532.11 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987307B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-43a0ddffbc024bcebd37a3e691cd7d7b |
| Source note | uspto-grants-2015_03 |