Pyridine → HCID 66893845, compound

Participants

Reaction Steps

2-Chlorobenzenesulfonyl chloride (76.0 mg, 0.36 mmol) and pyridine (219 mL) were added to tert-butyl[1-(5-amino-1-benzofuran-7-yl)piperidin-4-yl]carbamate (100.0 mg, 0.30 mmol; Intermediate 49) in DCM (1 mL). The mixture was shaken at room temperature for 1 h, solvent was removed in vacuo and the residue was purified by preparative HPLC using acetonitrile-water gradients containing 0.1% trifluoroacetic acid. N-deprotection and conversion into the hydrochloride salt was performed by treatment with 2 M HCl in ether. This furnished to 60.6 mg (50%) of the title product. HPLC 100%, RT: 1.702 (System A; 10-97% MeCN over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.69-1.72 (m, 2H) 2.01-2.02 (m, 2H) 2.76 (t, J=11.62 Hz, 2H) 3.21 (s, 1H) 3.68 (d, J=12.56 Hz, 2H) 6.58 (s, 1H) 6.82 (d, J=2.20 Hz, 1H) 6.88 (s, 1H) 7.47 (t, J=7.54 Hz, 1H) 7.62-7.63 (m, 2H) 7.87 (d, J=1.88 Hz, 1H) 7.99 (d, J=7.54 Hz, 1H) 8.23 (s, 3H) 10.33 (s, 1H). LC-MS 406 (M+H)+.

Provenance & Evidence