Pyridine → HCID 66894250, compound

Participants

Reaction Steps

2-Methoxy-5-methylbenzenesulfonyl chloride (80.0 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 59.0 mg (47%) of the title product. HPLC 100%, RT: 1.731 (System A; 10-97% MeCN over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.70-1.76 (m, 2H) 2.05 (d, J=10.05 Hz, 2H) 2.20 (s, 3H) 2.76 (t, J=11.46 Hz, 2H) 3.19-3.21 (m, 1H) 3.65 (d, J=12.56 Hz, 2H) 3.87 (s, 3H) 6.58 (d, J=1.88 Hz, 1H) 6.81 (d, J=2.20 Hz, 1H) 6.89 (d, J=1.88 Hz, 1H) 7.04 (d, J=8.48 Hz, 1H) 7.32 (dd, J=8.48, 2.20 Hz, 1H) 7.51 (d, J=2.20 Hz, 1H) 7.86 (d, J=1.88 Hz, 1H) 8.35 (d, J=3.45 Hz, 3H) 9.65 (s, 1H). LC-MS 416 (M+H)+.

Provenance & Evidence