Triethylamine → HCID 178454277, compound

Participants

Reaction Steps

Mercury (II) chloride (192 mg, 0.707 mmol) was added in one portion to a stirred mixture of 3-aminoisoquinoline (84.5 mg, 0.586 mmol), N,N′-di-t-butoxycarbonyl-S-methylisothiourea (Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700-1703) (204 mg, 0.703 mmol), and triethylamine (250 μL, 1.79 mmol) in CH2Cl2 (3.0 mL) under N2 at 23° C. The mixture was stirred for 26 hours and then directly purified by column chromatography upon silica gel using hexanes-EtOAc (98:2 to 95:5) as eluant to give 3-(N′,N″-di-t-butoxycarbonyl-N-guanidinyl)isoquinoline (189.4 mg, 0.492 mmol) as a white solid.

Provenance & Evidence