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

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Reaction Steps

A solution of 2-chlorobenzenesulfonic acid 3-[(piperazin-4-yl)ethoxy]phenyl ester (397 mg, 1.0 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) in DMF (10 mL) was stirred at room temperature overnight. The DMF was removed in vacuo and residue was purified by flash column chromatography (85:15:2 methylene chloride:methanol:acetic acid) to give the title compound as a white solid (290 mg, 52%). 1H-NMR (300 MHz, CDCl3 /CD3OD) δ 2.01 (bs, 6H), 2.64 (t, 4H), 2.84 (t, 2H), 3.45 (t, 4H), 4.07 (t, 2H), 6.67 (dd, 1H), 6.77 (t, 1H), 6.83 (dd, 1H), 7.19 (t, 1H), 7.41 (dt, 1H), 7.65 (t, 2H), 7.95 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C19H23 N4O4SCl: 439.1(M+H), 461.1 (M+Na). Found: 438.8, 460.8.

Provenance & Evidence