Methylamine → HCID 67280509, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (32 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 (57 mg), dichloroethane (1 ml), a 2 N solution of methylamine in tetrahydrofuran (0.2 ml) and acetic acid (23 μl), and the mixture was stirred at room temperature overnight. Methanol (one drop) was added dropwise to the reaction mixture, and then a 0.2 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) was added to the resulting residue, and pyridine (24 μl) and acetyl chloride (14 μl) were added dropwise under ice-cooling. 4-Dimethylaminopyridine (1 mg) was added and the mixture was stirred under ice-cooling for 10 minutes and at room temperature for three hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (ethyl acetate), and then the title compound (19 mg, 79%) was obtained as an oil in the same manner as in Example 2.

Provenance & Evidence