o-Toluenesulfonyl chloride → 2-Methyl-N-{7-[(2-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide dihydrochloride

Participants

Reaction Steps

The title product was prepared according to the procedure of Example 112, Step 3, starting from tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-3-methylpiperazine-1-carboxylate (45 mg crude material, 0.10 mmol; obtained in Example 112, Step 2) and o-toluenesulfonyl chloride (22 μL, 0.15 mmol). The title compound (17 mg, 35%) was obtained as an off-white solid. HPLC 99%, 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 1.69-1.74 (m, 3H) 2.67 (s, 3H) 3.37-3.62 (m, 5H) 3.67-3.75 (m, 1H) 3.84-3.95 (m, 1H) 4.57-4.65 (m, 1H) 4.90-4.97 (m, J=13.55 Hz, 1H) 6.86 (d, J=2.26 Hz, 1H) 7.23-7.29 (m, J=7.65, 7.65 Hz, 1H) 7.31 (d, J=2.01 Hz, 1H) 7.32-7.36 (m, 1H) 7.40-7.46 (m, 1H) 7.50 (d, J=2.01 Hz, 1H) 7.85-7.90 (m, 2H). MS (ESI+) for C21H25N3O3S m/z 400 (M+H)+.

Provenance & Evidence