Diisopropylethylamine → N-((2'-methyl-[2,4'-bipyridin]-5-yl)methyl)-4-(pyrazin-2-yl)benzamide

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Reaction Steps

To a mixture of (2′-methyl-[2,4′-bipyridin]-5-yl)methanamine 18-2 (10.0 mg, 0.05 mmol), 4-(pyrazin-2-yl)benzoic acid 18-3 (10.0 mg, 0.05 mmol), and HATU (23 mg, 0.06 mmol) were added N,N-diisopropylethylamine (DIEA, 17 μL, 0.1 mmol) and DMF (0.5 mL). The solution was stirred overnight at room temperature and was subjected directly to reverse phase preparative HPLC to yield N-42′-methyl-[2,4′-bipyridin]-5-yl)methyl)-4-(pyrazin-2-yl)benzamide 18 as a white powder. MS m/z 382.2 (M+1). 1H NMR 400 MHz (CDCl3) δ 9.06 (d, 1H), 8.73 (d, 1H), 8.66 (dd, 1H), 8.59 (d, 1H), 8.56 (d, 1H), 8.15-8.08 (m, 2H), 8.00-7.91 (m, 2H), 7.86 (dd, 1H), 7.80-7.73 (m, 2H), 7.65 (dd, 1H), 6.90 (t, 1H), 4.76 (d, 2H), 2.64 (s, 3H).

Provenance & Evidence