Benzoyl isothiocyanate → (6,7-Dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

참여 물질

반응 단계

(4-Amino-6,7-dimethoxy-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (277 mg, 0.831 mmol) was dissolved in dry acetone, and benzoylisothiocyanate (149 mg, 0.914 mmol) was added dropwise. The reaction was stirred at room temperature for 2 h, and was concentrated to yield a yellow solid. This solid was triturated with 50% aqueous EtOH, filtered, and suspended in 10% NaOH (5.0 mL). The reaction mixture was placed in an oil bath that was pre-heated to 98° C. for 1 h, (the solid was dissolved in 10 min). The mixture was cooled and filtered. The yellow solid was washed with water, and dried in vacuo to give (6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (165 mg; 51%). 1H-NMR (CDCl3): δ, 8.31 (s, 1H), 7.66 (s, 1H), 7.38 (s, 1H), 4.81 (s, 2H), 4.05 (s, 3H), 4.00 (s, 3H), 2.81 (s, 2H), 1.46 (s, 9H); MS: calculated for C18H24N4O4S+H 393.0; found: 392.9.

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