Dimethylformamide → HCID 67279747, compound

Participants

Reaction Steps

Sodium hydride (6.7 mg) was added to a mixture of di-tert-butyl {8-hydroxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 32 (40 mg) and dehydrated N,N-dimethylformamide (1 mL), and then the mixture was stirred at room temperature for one hour. Methyl iodide (6.5 μL) was added to the reaction mixture, followed by stirring for 1.5 hours. Then, water (20 mL) was added. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. After filtration, 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 to obtain the title compound (4.8 mg, 18%) as a solid.

Provenance & Evidence