HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → N-[6-Chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid | HCID 21544516 | — |
| Reactant | [6-Chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine | HCID 86670794 | — |
| Product | N-[6-Chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide | HCID 86670793 | 61% |
Reaction Steps
The title compound was prepared in analogy to Example 90, from [6-chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine and 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (example 114, intermediate a) after a reaction time of 17 hours. The compound was purified by silica gel chromatography using an MPLC (ISCO) system eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50). The volatiles were evaporated until a precipitate formed. The suspension was filtered and the filter cake was washed three times with a small amount of a mixture of EtOAc:n-heptane (1:4) to give the title compound as a colorless solid (61%). MS (ESI): m/z=517.06 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987307B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-0a8a2a87c2f141378e3411f1284e8993 |
| Source note | uspto-grants-2015_03 |