Hydrochloric Acid → HCID 178512151, compound

Participants

Reaction Steps

One gram (2.66 mmol) of free amine was stirred with 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (1.55 g, 3.99 mmol) in dry ethanol (25 mL). Di-isopropyl-ethylamine (1.39 mL, 7.98 mmol) of was added and the reaction mixture was warmed to 45° C. overnight. Ethanol was added and the reaction filtered. After concentration of the filtrate, the residue was purified by flash chromatography (0-10% MeOH/CH2Cl2) to give 0.92 g of [3-(4-{4-[N′-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-guanidino]-butyl}-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester. [3-(4-{4-[N′-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-guanidino]-butyl}-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester (2.7 g was stirred with 4M HCl in p-dioxane for 1 hour at room temperature. Solvents were removed in vacuo.

Provenance & Evidence