Ethanol → Ethyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate

Participants

Reaction Conditions

Reaction Steps

A reaction mixture containing 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]-amino}benzoic acid (21 mg, 0.055 mmol) (Intermediate 19), 1,1′-carbonyldiimidazole (17 mg, 0.106 mmol) and pyridine (9 μL, 0.113 mmol) in MeCN (0.75 mL) was stirred at 60° C. for 30 min, and then a second portion of pyridine (5 μL, 0.062 mmol) was added. After additional 30 min of stirring at 60° C., EtOH (6 μL, 0.100 mmol) was added. The reaction mixture was stirred at 50° C. over night, and then diluted with DMSO/MeCN/water. TFA (50 μL) was added and the crude product was purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, gradient: 0.1% TFA in water/MeCN over 6 minutes). The title compound was obtained in 54% yield (12.2 mg). 1H NMR (500 MHz, CDCl3) δ ppm 1.34 (t, J=7.08 Hz, 3 H) 2.45 (s, 3 H) 4.33 (q, J=7.08 Hz, 2 H) 6.92 (s, 1 H) 7.36 (dd, J=8.04, 7.66 Hz, 1 H) 7.42 (ddd, J=8.04, 2.32, 1.17 Hz, 1 H) 7.44 (dd, J=8.70, 1.95 Hz, 1 H) 7.71 (d, J=8.70 Hz, 1 H) 7.71 (d, J=1.95 Hz, 1 H) 7.71-7.72 (m, 1 H) 7.84 (ddd, J=7.66, 1.48, 1.17 Hz, 1 H). MS (ESI+) m/z 410 [M+H]+.

Provenance & Evidence