Diisopropylethylamine → 5-(4-Acetylpiperazin-1-yl)-N-((3-methyl-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methyl)picolinamide

Participants

Reaction Steps

To a mixture of (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 48-1 (27 mg, 0.10 mmol), 5-(4-acetylpiperazin-1-yl)picolinic acid 48-2 (25 mg, 0.10 mmol) and HATU (38 mg, 0.10 mmol) in DMF (0.6 mL) was added DIEA (0.08 mL, 0.50 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 5-(4-acetylpiperazin-1-yl)-N-((3-methyl-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methyl)picolinamide 48 as a white powder. MS m/z 499.20 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 9.20 (t, 1H, J=6.4 Hz), 8.86 (d, 1H, J=5.2 Hz), 8.53 (m, 1H), 8.32 (d, 1H, J=2.8 Hz), 8.04 (s, 1H), 7.93-7.86 (m, 2H), 7.72 (m, 1H), 7.43 (dd, 1H, J1=8.8 Hz, J2=2.8 Hz), 4.52 (d, 2H, J=6.4 Hz), 3.60-3.58 (m, 4H), 3.41-3.38 (m, 4H), 2.36 (s, 3H), 2.05 (s, 3H).

Provenance & Evidence