Diisopropylethylamine → N-((2',5-dimethyl-3,4'-bipyridin-6-yl)methyl)-5-(pyrazin-2-yl)picolinamide

Participants

Reaction Steps

To a mixture of 5-(pyrazin-2-yl)picolinic acid 41-4 (20 mg, 0.1 mmol), (2′,5-dimethyl-3,4′-bipyridin-6-yl)methanamine 81-5 (21 mg, 0.1 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (38 mg, 0.1 mmol) in DMF (1.0 mL) was added DIEA (0.053 mL, 0.3 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted into DMSO and purified by HPLC to give N-42′,5-dimethyl-[3,4′-bipyridin]-6-yl)methyl)-5-(pyrazin-2-yl)picolinamide 81 as a white solid. MS m/z 397.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.60 (t, 1H), 9.54 (d, 1H), 9.52 (d, 1H), 8.99 (d, 1H), 8.91 (m, 1H), 8.82-8.80 (m, 2H), 8.66 (d, 1H), 8.33 (d, 1H), 8.20 (d, 1H), 7.87 (s, 1H), 7.79 (b, 1H), 4.81 (d, 2H), 2.64 (s, 3H), 2.51 (s, 3H).

Provenance & Evidence