Phenacyl bromide → [6,7-Dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

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A solution of (6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (50 mg, 0.127 mmol) and 2-bromoacetophenone (27.9 mg, 0.140 mmol) in acetone (1.4 mL) in a conical vial was added MgSO4 (7.7 mg, 0.0637 mmol). The resulting suspension was placed in an aluminum block preheated to 60° C. and was allowed to stir for 3.0 h. The reaction was cooled and concentrated. The residue was purified using a 5.0 g silica cartridge (MeOH/CH2Cl2, 1:99) to give [6,7-dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester as a yellow solid (44.6 mg; 71%). 1H-NMR (CDCl3): δ, 8.64 (s, 1H), 7.52-7.41 (m, 6H), 6.76 (s, 1H), 6.17 (s, 1H), 4.92 (d, 2H, J=4.7 Hz), 4.06 (s, 3H), 4.02 (s, 3H), 1.51 (s, 9H); MS: calculated for C26H28N4O4S+H 493.5; found: 493.5.

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