Hydrochloric Acid → 2,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide

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Reaction Steps

Lithium aluminium hydride (216 mg, 5.7 mmol) was added to a stirred solution of 2-(2,4-dichloro-benzenesulfonylamino)-N-methoxy-N-methyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinamide (368 mg, 0.57 mmol) in THF (30 ml) and the reaction stirred for 90 minutes at room temperature. 1N HCl solution (10 ml) was added cautiously and following 10 minutes of stirring NaHCO3 solution (40 ml) was added. The aqueous solution was extracted with ethyl acetate (2×40 ml), the combined extracts dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography using ethyl acetate 2/3 hexane as eluent to afford 2,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide as a yellow oil (130 mg, 39%). 1H NMR (CDCl3); 10.25 (1 H, s, COH); 8.53 (1 H, s, py); 8.17 (1 H, d, Ar); 7.57 (2 H, d, Ar); 7.51 (1 H, s, Ar); 7.42 (2 H, m, py and Ar); 7.21 (2 H, d, Ar); 2.89 (4 H, m, 2×CH2N pip); 1.55 (4 H, m, 2×CH2 pip); 1.34 (2 H, m, CH2 pip).

Provenance & Evidence