Acetonitrile → HCID 86687648, compound

Participants

Reaction Steps

A vial was charged with perfluorophenyl 1-(3′,5′-difluoro-3-methoxy-[1,1′-biphenyl]-4-yl)isoquinoline-6-sulfonate (INTERMEDIATE KKKKK; 50.05 mg, 0.084 mmol), 1,3,4-oxadiazol-2-amine (7.89 mg, 0.093 mmol), cesium carbonate (82 mg, 0.253 mmol), and acetonitrile (0.42 mL). After 3 h or stirring, the mixture was diluted with 0.5 N aq. HCl, then extracted with EtOAc (3×), 20% MeOH/EtOAc (2×), and DCM (1×). The combined organic extracts were concentrated. The residue was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 0-7% MeOH/DCM) to give 1-(3′,5′-difluoro-3-methoxy-[1,1′-biphenyl]-4-yl)-N-(1,3,4-oxadiazol-2-yl)isoquinoline-6-sulfonamide (19.1 mg, 0.039 mmol, 45.8% yield) as a white foam. 1H NMR (400 MHz, DMSO-d6) δ=12.24 (br. s., 1H), 8.82 (d, J=2.0 Hz, 1H), 8.78 (d, J=5.7 Hz, 1H), 8.23 (d, J=5.3 Hz, 1H), 8.17 (s, 1H), 8.00-7.94 (m, 1H), 7.92-7.84 (m, 1H), 7.68-7.60 (m, 2H), 7.58-7.49 (m, 2H), 7.47-7.41 (m, 1H), 7.30 (tt, J=2.3, 9.3 Hz, 1H), 3.78 (s, 3H). m/z (ESI) 495.1 (M+H)+.

Provenance & Evidence