3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-oxazol-2-ylmethyl-5-trifluoromethyl-benzamide

Participants

Reaction Steps

The title compound was prepared in analogy to example 90, from [4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-oxazol-2-ylmethyl-amine and 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (example 144, intermediate a) after a reaction time of 72 hours. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The product-containing fractions were pooled and evaporated. The remaining red solid was purified by preparative HPLC (Gemini NX) with a gradient of methanol:water containing 0.05% formic acid (80:20 to 98:2). Colorless foam (41%). MS (ESI): m/z=550.105 [M+H]+.

Provenance & Evidence