Chloroacetone → [6,8-Dimethoxy-4-(4-methyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

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To solution of (6,8-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (50 mg, 0.127 mmol) and chloroacetone (16.1 mg, 0.166 mmol) in acetone (1.4 mL) was added MgSO4 (7.7 mg, 0.0637 mmol). The resulting suspension was stirred at 60° C. and for 4.5 h. The reaction was cooled and concentrated. The residue passed through a 5 g silica cartridge, eluting with 2% MeOH in DCM, to give [6,8-dimethoxy-4-(4-methyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester as a yellow solid (21.3 mg; 39%). 1H-NMR (CDCl3): δ, 8.59 (s, 1H), 7.00 (s, 1H), 6.76 (s, 1H), 6.61 (d, 1H, J=2.2 Hz), 6.13 (s, 1H), 5.05 (d, 2H, J=4.3 Hz), 3.99 (s, 3H), 3.92 (s, 3H), 2.32 (s, 3H), 1.51 (s, 9H); MS: calculated for C21H26N4O4S+H 431.0; found: 431.0.

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