3,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide → {2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[3-(4-{3-[4-((S)-2,3-dihydroxy-propoxy)-phenyl]-propoxy}-phenyl)-propyl]-dimethyl-ammonium bromide

Participants

Reaction Steps

3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid (2-dimethylamino-ethyl)-amide (Intermediate H) (0.65 g, 2.52 mmol) and (S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol (Intermediate J) (1.60 g, 3.78 mmol) in butan-2-one (25 mL) is heated at reflux overnight during which time precipitation of white solid is observed. The reaction mixture is filtered to collect the product, washed with warm acetone and dried under vacuum to afford the title compound. M+ 601. 1H NMR (400 MHz, DMSO-d6) δ 8.29 (1H, t), 7.30 (1H, br), 7.12 (2H, d), 7.11 (2H, br), 7.07 (2H, d), 6.95 (1H, br), 6.84 (2H, d), 6.82 (2H, d), 4.89 (1H, d), 4.63 (1H, t), 3.94 (1H, dd), 3.89 (2H, t), 3.81 (1H, dd), 3.77 (1H, m), 3.59 (2H, m), 3.43 (2H, m), 3.42 (2H, m), 3.34 (2H, m), 3.08 (6H, s), 2.66 (2H, m), 2.47 (2H, m), 1.96 (2H, m), 1.93 (2H, m).

Provenance & Evidence