2-Chlorobenzenesulfonyl chloride → 2-Chloro-N-{7-[(3-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide, dihydrochloride

Participants

Reaction Steps

The title compound was prepared according to the procedure of Example 115, Step 4, starting from tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-2-methylpiperazine-1-carboxylate (41 mg crude starting material, 0.11 mmol; obtained in Example 115, Step 3) and 2-chlorobenzenesulfonyl chloride (22 μL, 0.17 mmol). The title compound (21 mg, 39%) was obtained as an off-white solid. HPLC 100%, RT=1.42 min (System A; 10-97% MeCN over 3 min), 100%, RT=1.26 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 1.41 (d, J=6.53 Hz, 3H) 3.32-3.37 (m, 1H) 3.45-3.59 (m, 2H) 3.63-3.76 (m, 3H) 3.78-3.89 (m, 1H) 4.70 (s, 2H) 6.86 (d, J=2.26 Hz, 1H) 7.36-7.41 (m, 1H) 7.42 (d, J=2.01 Hz, 1H) 7.49-7.54 (m, 1H) 7.54-7.58 (m, 2H) 7.86 (d, J=2.01 Hz, 1H) 8.02 (dd, J=7.91, 1.63 Hz, 1H). MS (ESI+) for C20H22ClN3O3S m/z 420 (M+H)+.

Provenance & Evidence