Diisopropylethylamine → 2-Chlorobenzenesulfonic acid 3-[2-[1-(aminoiminomethyl)piperazin-4-yl]ethoxy]-5-methylphenyl ester diacetic acid salt

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Reaction Steps

A solution of 2-chlorobenzenesulfonic acid 3-[2-(piperazin-4-yl)ethoxy]-5-methylphenyl ester (411 mg, 1.0 mmol), as prepared in the preceding step, in DMF (10 mL) containing N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) was stirred at room temperature overnight. The DMF was removed in vacuo and the residue was purified by flash column chromatography (85:15:2 methylene chloride:methanol:acetic acid) to give the title compound as a white solid (295 mg, 51%). 1H-NMR (300 MHz, CDCl3) δ 1.95 (s, 6H), 2.23 (s, 3H), 2.61 (t, 4H), 2.78 (t, 2H), 3.48 (t, 4H), 3.99 (t, 2H), 6.52 (s, 2H), 6.59 (s, 1H), 7.39 (dt, 1H), 7.62 (m, 2H), 7.96 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C20H25N4O4SCl: 453.1(M+H), 475.1 (M+Na). Found: 452.7, 474.9.

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