m-Chloroperbenzoic acid → 2-[4-[2-(Benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-n-[2-methanesulfinyl-6-methyl-4-(methylthio)-3-pyridyl]-acetamide

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Reaction Steps

To a mixed solution of this amide (500 mg, 0.664 mmol) in chloroform (10 ml) and methanol (2 ml) was added m-chloroperbenzoic acid (213 mg, 1.23 mmol) with ice-cooling, and stirred at room temperature for 26 hours. The reaction solution was diluted with chloroform. The organic layer was washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=10:1) to provide 138 mg (yield 40%) of the desired compound as colorless amorphous. IR (neat) cm−1: 3424, 3155, 1695, 1571, 1481. 1H-NMR (d6-DMSO, 120° C.) δ: 2.51 (3H, s), 2.56 (3H, s), 2.73,(3H, s), 2.59-2.68 (6H, m), 2.77 (2H, t, J=7.1 Hz), 2.81-2.92 (2H, br s), 3.11 (1H, d, J=15.8 Hz), 3.17 (1H, d, J=15.8 Hz), 3.41 (2H, t, J=7.1 Hz), 7.07-7.13 (2H, m), 7.30 (1H, S), 7.38-7.44 (2H, m), 9.26 (1H, br s).

Provenance & Evidence