Pyridine → HCID 66892783, compound

Participants

Reaction Steps

2-(Trifluoromethyl)benzenesulfonyl chloride (89.0 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 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 76.1 mg (57%) of the title product. HPLC 100%, RT: 1.834 (System A; 10-97% MeCN over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.70-1.72 (m, 2H) 2.00-2.02 (m, 2H) 2.78 (t, J=11.30 Hz, 2H) 3.21 (s, 1H) 3.71 (d, J=12.56 Hz, 2H) 6.60 (d, J=1.88 Hz, 1H) 6.83 (d, J=2.20 Hz, 1H) 6.85-6.91 (m, J=1.88 Hz, 1H) 7.80-7.81 (m, 2H) 7.88-7.89 (m, 1H) 7.96-7.98 (m, 1H) 8.08-8.10 (m, 4H) 10.40 (s, 1H). LC-MS 440 (M+H)+.

Provenance & Evidence