Trifluoroacetic acid → HCID 59490392, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-ylcarbamate (3.0 g, 8.8 mmol) in dichloromethane (30 mL) was added trifluoroacetic acid (10 mL). The reaction was stirred at room temperature for 3 hours. The solvent was then removed under reduced pressure to give an oily residue that was triturated in diethyl ether to give a solid. The solid was filtered, washed with diethyl ether and dried under reduced pressure to give the desired product 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-ylamine (TFA salt) as a brown solid (2.1 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 8.08 (bs, 2H), 8.07 (s, 1H), 8.02 (s, 1H), 7.161 (d, 2H, J=8.4 Hz), 6.84 (d, 2H, J=8.8 Hz), 5.53 (s, 2H), 3.69 (s, 3H), 3.67-3.52 (m, 1H) 3.23 (dd, J=4.4, 16 Hz, 1H), 3.16-3.04 (m, 2H), 2.930 (dd, J=9.6, 15.6 Hz, 1H), 2.19-2.29 (m, 1H), 1.85-1.98 (m, 1H). LCMS [M+H]: 309.

Provenance & Evidence