Hydrochloric Acid → HCID 66892013, compound

Participants

Reaction Steps

To the obtained 7-(3-methyl-piperazin-1-carbonyl)-benzofuran-5-sulfonic acid (2-methoxy-5-methyl-phenyl)-amide (30 mg, 0.07 mmol; Step 1) was added LiAlH4 (9.0 mg, 0.24 mmol) in dry THF (4 mL) and the mixture was warmed to reflux. After 1 h, HPLC analysis showed 15% product and the remaining impurities. Added mixture to 2 M HCl, concentrated and purified by preparative HPLC (Gilson; gradient of 30-70% MeCN). The pure fractions were stripped, HCl/ether added and concentrated to give the title compound as a colourless solid. Yield: 1.3 mg (5%). HPLC 90% RT=1.17 min (System A; 30-80% MeCN over 3 min), 1.13 min (System C; 2-95% MeCN over 2 min). 1H NMR (400 MHz, methanol-d4) δ ppm 1.29 (d, J=7.0 Hz, 2H) 2.21 (s, 3H) 2.72 (m, 1H) 2.86 (m, 1H) 3.38 (s, 4H) 3.43-3.64 (m, 4H) 4.30 (d, J=6.59 Hz, 2H) 6.62 (d, J=8.30 Hz, 1H) 6.81-6.88 (m, 1H) 6.99 (d, J=2.44 Hz, 1H) 7.25 (d, J=1.95 Hz, 1H) 7.76 (br s, 1H) 7.94 (d, J=2.20 Hz, 1H) 8.08 (d, J=1.71 Hz, 1H). MS (ESI) for C22H27N3O4S m/z 430 (M+H).

Provenance & Evidence