Isopropylamine → HCID 86641333, compound

Participants

Reaction Steps

Isopropylamine (5.5 μl) was added to a mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 40 (30 mg), methanol (0.4 ml), tetrahydrofuran (0.2 ml) and acetic acid (12 μl), and then the mixture was stirred at room temperature for two hours. A solution of sodium cyanoborohydride (10 mg) in methanol (0.4 ml) was added to the reaction mixture, followed by stirring at room temperature overnight. The reaction mixture was concentrated, and a 0.2 N sodium hydroxide solution was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. Dichloromethane (1 ml) and trifluoroacetic acid (0.25 ml) were added to the resulting residue, and the mixture was stirred at room temperature for five hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by NH silica gel chromatography (chloroform-methanol). The resulting oil was dissolved in dioxane, followed by lyophilization to obtain the title compound (6.3 mg, 29%) as an amorphous.

Provenance & Evidence