Potassium Carbonate → HCID 67279889, compound

Participants

Reaction Conditions

Reaction Steps

A mixture composed of 4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-ylmethanesulfonate of Example 35 (65 mg), dehydrated N,N-dimethylformamide (1 mL) and potassium carbonate (14 mg) was heated with stirring at 70° C. for six hours. The reaction mixture was cooled and a saturated sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Dichloromethane (2 mL) and trifluoroacetic acid (1 mL) were added to the resulting residue, and the mixture was stirred at room temperature for one hour. After confirming that the raw material disappeared, the reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol) to obtain the title compound (12.9 mg, 36%) as a solid.

Provenance & Evidence