Dimethylamine → 1-{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-yl}-n,n-dimethylmethanamine

Participants

Reaction Steps

To a solution of Example 77 (115 mg; 0.29 mmol; 1 eq.) in DCM (6 mL) is added at 0° C. N-ethyldiisopropylamine (250 μL; 1.47 mmol; 5 eq.) and methanesulfonyl chloride (27 μL; 0.35 mmol; 1.2 eq.). After 15 min, dimethylamine (2M; 440 μL; 0.88 mmol; 3 eq.) was added and the reaction mixture stirred at room temperature for 2 hours. Water (5 mL) was added and the organic layer washed with water. The organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by mass triggered preparative HPLC (increasing amount of ACN in water) to afford the title compound as a brown oil.

Provenance & Evidence