Hydrochloric Acid → 2-(2,4-Dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid

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Reaction Steps

A solution of 2-(2,4-dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester (217 mg, 0.32 mmol) and lithium hydroxide monohydrate (54 mg, 1.3 mmol) in THF (15 ml) and water (15 ml) was stirred at 30° C. overnight. The reaction was diluted with water (25 ml), acidified to pH 1 with 1N HCl and extracted with ethyl acetate (2×30 ml). The combined extracts were dried (MgSO4) and concentrated under reduced pressure to give 2-(2,4-dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid as a yellow solid (173 mg, 90%). 1H NMR (CDCl3): 8.06 (1 H, d, Ar); 7.96 (1 H, s, Ar); 7.82 (1 H, s, py); 7.67 (3 H, m, py and Ar); 7.39 (3 H, m, Ar); 2.94 (4 H, m, 2×CH2N pip); 1.56 (4 H, m, 2×CH2 pip); 1.39 (2 H, m, CH2 pip).

Provenance & Evidence