Allyl bromide → HCID 86656629, compound

Participants

Reaction Steps

To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (2-{bis-[3-(4-methoxy-phenyl)-propyl]-amino}-ethyl)-amide trifluoroacetate (Intermediate D) (0.20 g, 0.31 mmol) in acetone (5 mL) is added sodium carbonate (99 mg, 0.94 mmol) followed by allyl bromide (0.082 mL, 0.94 mmol). The reaction mixture is heated at reflux for 72 h, cooled to RT then filtered to remove inorganic salts. The filtrate is concentrated and purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA) affords the title compound. M+ 567. 1H NMR (400 MHz, DMSO-d6) δ 8.32 (1H, t), 7.76 (2H, br), 7.16 (2H, br), 7.11 (4H, d), 6.85 (4H, d), 5.95 (1H, ddt) 5.62 (1H, d), 5.57 (1H, d), 3.99 (2H, d), 3.72 (6H, s), 3.58-3.54 (2H, m), 3.30 (2H, t), 3.24-3.20 (4H, m), 2.50 (4H, t), 1.97-1.78 (4H, m).

Provenance & Evidence