Diisopropylethylamine → N-((3-Methyl-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methyl)-4-(pyrazin-2-yl)benzamide

Participants

Reaction Steps

To a mixture of (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 48-1 (40 mg, 0.15 mmol), 4-(pyrazin-2-yl)benzoic acid 58-1 (30 mg, 0.15 mmol) and HATU (57 mg, 0.15 mmol) in DMF (0.9 mL) was added DIEA (0.08 mL, 0.45 mmol). The mixture was stirred at room temperature for 2 hours. The solvent was removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give N-((3-methyl-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methyl)-4-(pyrazin-2-yl)benzamide 58 as a white powder. MS m/z 450.20 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 9.35 (d, 1H, J=1.6 Hz), 9.30 (t, 1H, J=6.0 Hz), 8.86 (d, 1H, J=4.8 Hz), 8.76 (m, 1H), 8.67 (d, 1H, J=2.4 Hz), 8.57 (m, 1H), 8.30-8.27 (m, 2H), 8.08-8.06 (m, 3H), 7.94 (dd, 1H, J1=5.0 Hz, J2=1.2 Hz), 7.77 (m, 1H), 4.85 (d, 2H, J=6.0 Hz), 2.40 (s, 3H).

Provenance & Evidence