1,1-Dichloroethane → HCID 86641332, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (16 mg) 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 (34 mg), dichloroethane (0.7 ml), cyclobutylamine (15 μl) and acetic acid (10 μl), and the mixture was stirred at room temperature overnight. Methanol (three drops) was added dropwise to the reaction mixture, and then a 1 N sodium hydroxide solution was added, 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 (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue, and the mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by reversed phase liquid chromatography. The resulting oil was dissolved in dioxane, followed by lyophilization to obtain the title compound (6.3 mg, 25%) as a colorless amorphous.

Provenance & Evidence