Methylamine → HCID 67280840, compound

Participants

Reaction Steps

A mixture composed 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), dehydrated dichloromethane (1 mL), pyridine (11 μL) and triphosgene (8.7 mg) was stirred under cooling in an ice bath for three hours. A 2 N solution of methylamine in tetrahydrofuran (0.6 mL) was added to the reaction mixture. Then, the ice bath was removed and the mixture was stirred for 17 hours. After confirming that the raw material disappeared, the reaction mixture was diluted with chloroform and washed with water. The aqueous layer was extracted with chloroform, and then the combined organic layers were 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 15 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 (6.6 mg, 22%) as a solid.

Provenance & Evidence