Benzenesulfonyl chloride → HCID 67425880, compound

Participants

Reaction Steps

To a solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-ylamine TFA salt (0.156 g, 0.37 mmol) in anhydrous THF (5 mL) and Et3N (0.15 mL, 1.11 mmol) was added benzenesulfonyl chloride (60 μL, 0.46 mmol). The reaction mixture was shaken at room temperature for 3 hours followed by addition of EtOAc (20 mL) and 1.0M NaOH (15 mL). The organic layer was then separated, washed with brine (2×10 mL) and concentrated under reduced pressure to give the crude product. The crude product was purified using flash column chromatography (SiO2, 33% EtOAc in hexane) to give the desired product, N-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl)benzenesulfonamide as a white solid (0.103 g, 62%). Alternatively the crude product could be used in the next step without any further purification. M.p.>70° C.; 1H NMR (400 MHz, DMSO-d6) δ7.99 (s, 1H), 7.91 (s, 1H), 7.86 (m, 2H), 7.81 (s, 1H), 7.68-7.58 (m, 3H), 7.14 (m, 2H), 6.83 (m, 2H), 5.50 (s, 2H), 3.68 (s, 3H), 3.48 (m, 1H), 2.96 (m, 3H), 2.76 9m, 1H), 1.91 (m, 1H), 1.77 (m, 1H); LCMS [M+H]: 449.

Provenance & Evidence