Pyridine → N-(7-Pyrimidin-5-yl-1-benzofuran-5-yl)benzenesulfonamide hydrochloride

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Reaction Steps

Benzenesulfonyl chloride (0.093 g, 0.524 mmol) and pyridine (347 μL, 430 mmol) were added to 7-pyrimidin-5-yl-1-benzofuran-5-amine (0.100 g, 0.473 mmol; Intermediate 18) in dichloromethane (2 mL). The mixture was shaken at room temperature for 1 h and the solvent was removed. The crude product was purified by preparative HPLC using acetonitrile-water gradients containing 0.1% trifluoroacetic acid and then converted into the hydrochloride salt by treatment with 2 M HCL in diethyl ether. This gave 0.071 g (43%) of the title compound as a yellow solid. HPLC 97%, RT: 1.863 min (System A; 10-97% over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 6.98 (d, J=2.20 Hz, 1H) 7.34 (d, J=2.20 Hz, 1H) 7.50-7.54 (m, 3H) 7.58-7.60 (m, 1H) 7.80-7.82 (m, 1H) 7.97 (d, J=2.20 Hz, 1H) 9.10 (s, 2H) 9.20 (s, 1H) 9.87 (s, 1H). GC-MS 351 (M+).

Provenance & Evidence