HuagongsheHuagongshe Chemistry Print Report · For research reference only
[4-(2-Chloro-phenyl)-pyridin-3-yl]-methyl-amine → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | [4-(2-Chloro-phenyl)-pyridin-3-yl]-methyl-amine | HCID 18403335 | — |
| Reactant | 3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid | HCID 21544516 | — |
| Product | N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide | HCID 70663342 | 26% |
Reaction Steps
The title compound was prepared in analogy to example 90, from [4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine (prepared according to DE10008042) and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (example 114, intermediate a) after a reaction time of 18 hours at room temperature. The compound was purified by silica gel chromatography on a 20 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Another purification step using preparative HPLC (Gemini NX column) with a gradient of MeOH:water (containing 0.05% formic acid) (80:20 to 98:2) gave the desired compound as a colorless foam (26%). MS (ESI): m/z=469.060 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987307B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-b026c8e7a18643daa612f4f6f4b2d55f |
| Source note | uspto-grants-2015_03 |