1,1-Dichloroethane → HCID 86641327, compound

Participants

Reaction Steps

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 (170 mg), dichloroethane (2 mL), acetic acid (0.034 mL) and 2,4-dimethoxybenzylamine (0.073 mL) was stirred at room temperature for 10 minutes. Then, sodium triacetoxyborohydride (126 mg) was added and the mixture was stirred for two hours. Sodium triacetoxyborohydride (63 mg) was added to the reaction mixture, followed by further stirring for one hour. Methanol (three drops) was added dropwise to the reaction mixture, and then the mixture was separated with chloroform and a 0.5 N sodium hydroxide solution. The aqueous layer was extracted with chloroform, and then the combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol-chloroform) to obtain the title compound (108 mg, 50%) as an oil.

Provenance & Evidence