4-Chlorobenzenesulfonyl chloride → [5-(4-Chloro-benzenesulfonylamino)-pentyl]-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

Participants

Reaction Steps

A mixture of (5-amino-pentyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate O) (0.25 g, 0.59 mmol), 4-chlorobenzenesulfonyl chloride (0.13 g, 0.59 mmol) and N-methylmorpholine (0.30 mL, 2.73 mmol) in DMF (5 mL) is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and is purified by column chromatography (basic alumina, 0-10% MeOH in DCM). The solid that is obtained is dissolved in a minimum amount of MeOH and DCM then precipitated by the addition of diethyl ether. The supernatant solvent mixture is decanted and the product is washed again with diethyl ether then dried under vacuum to give the title compound. M+ 578. 1H NMR (400 MHz, DMSO-d6) δ 8.25 (1H, t), 7.78 (2H, d), 7.74 (1H, t), 7.57 (2H, br), 7.67 (2H, d), 7.11 (2H, br), 3.56 (2H, q), 3.36 (2H, t), 3.28-3.22 (2H, m), 3.04 (6H, s), 2.95 (2H, q), 1.65-1.58 (2H, m), 1.37 (2H, quintet), 1.24-1.16 (2H, m).

Provenance & Evidence