Hydrochloric Acid → 2-(1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-N-(4-methoxy-benzyl)-acetamide

Participants

Reaction Steps

To a solution of {6,7-dimethoxy-4-[(4-methoxy-benzylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester (64 mg, 0.13 mmol) in 1.5 mL of EtOAc was added 3 mL of a 4 M solution of HCl in dioxane. After stirring at room temperature for 1 h, 1 mL of EtOH was added to facilitate solution. The reaction was stirred for 48 hours and the precipitated HCl salt was collected by filtration (58 mg, >100%). H1-NMR (DMSO): 9.00 (m, 1H), 8.79 (br s, 3H), 8.35 (s, 1H), 7.62 (s, 1H), 7.46 (s, 1H), 7.12 (d, J=8.5 Hz, 2H), 6.80 (d, 2H, J=8.3 Hz), 4.75 (br s, 2H), 4.18 (d, J=5.4 Hz, 2H), 4.02 (s, 3H), 4.00 (s, 2H), 3.82 and 3.68 (s, 3H); MS: APCI (M+H) calc'd for C22H25N3O4+H 396.5; found 396.2.

Provenance & Evidence