5-Chloro-2-methoxybenzene-1-sulfonyl chloride → HCID 68695652, compound

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Reaction Steps

A solution of 4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid ethyl ester (140 mg, 0.43 mmol) in dichloromethane (5 ml) and pyridine (0.15 ml) was treated with 5-chloro-2-methoxy-benzenesulfonyl chloride (159 mg, 0.66 mmol, 1.5 equiv.) and stirred at room temperature for 17 hours. The solvent was then evaporated and the residue purified by flash chromatography (dichloromethane/ether 9:1) to yield 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid ethyl ester as a white foam, 227 mg (100%). MS (ISP): m/e=527.2 (M−H); δH (300 MHz; d6-DMSO) 10.5 (1H, s), 8.02 (1H, d), 7.96 (2H, d), 7.93 (2H, d), 7.85 (1H, d), 7.72 (1H, dd), 7.67 (1H, dd), 7.30 (1H, d), 7.23 (1H, d), 4.30 (2H, q), 3.78 (2H, m), 2.75 (2H, t), 1.74 (2H, m), 1.32 (3H, t).

Provenance & Evidence