4-Methylmorpholine → {4-[2-(4-Benzyloxy-phenyl)-acetylamino]-butyl}-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

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Reaction Steps

To a solution of 4-Benzyloxyphenyl acetic acid (0.013 g, 0.30 mmol) in DMF (1.5 mL) is added HATU (0.12 g, 0.3 mmol), N-methylmorpholine (0.13 mL, 1.2 mmol) and (4-amino-butyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate N) (0.1 g, 0.30 mmol). The solution is stirred at RT for 2 h. The solvent is removed in vacuo and the residue is purified by reverse phase chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA) to yield the title compound. M+ 535. 1H NMR (400 MHz, DMSO-d6) δ 8.25 (1H, t), 8.05 (1H, t), 7.25 (2H, br), 7.42-7.32 (5H, m), 7.17 (2H, d), 7.09 (2H, br), 6.92 (2H, d), 5.06 (2H, s), 3.61-3.53 (2H, m), 3.39-3.33 (4H, m), 3.32 (2H, s), 3.10-3.03 (2H, m), 3.02 (6H, s), 1.61-1.49 (2H, m), 1.44-1.33 (2H, m).

Provenance & Evidence