p-(Methylsulphonyl)benzoic acid → 7-Chloro-3-[(4-methanesulfonyl-benzoylamino)-methyl]-4-oxo-1-phenyl-1,4-dihydro-quin-oline-2-carboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 4-(methanesulfonyl)benzoic acid (50.2 mg, 0.251 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (140 mg, 0.301 mmol) N,N-diisopropylethylamine (162 mg, 1.25 mmol) and CH2Cl2 (10 mL) was stirred at room temperature for 5 min. After this time, 3-aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester hydrochloride (intermediate I) (95 mg, 0.251 mmol) was added. The reaction mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated and purified by preparative reverse-phase HPLC, providing 7-chloro-3-[(4-methanesulfonyl-benzoylamino)-methyl]-4-oxo-1-phenyl-1,4-dihydroquin-oline-2-carboxylic acid methyl ester. MS calcd. for C26H22ClN2O6S [(M+H)+] 525.1, obsd. 525.0.

Provenance & Evidence