Methyl iodide → HCID 67350924, compound

Participants

Reaction Steps

(S)-5-[5-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)nicotinic acid (200 mg, 0.538 mmol) obtained in Step 2 was dissolved in dichloromethane (5 mL), and the mixture was stirred at room temperature for 30 minutes after adding 1,1′-carbonyldiimidazole (96.0 mg, 0.592 mmol). The mixture was further stirred for 3 hours after adding hydrazine.monohydrate (0.0780 mL, 1.62 mmol), and concentrated under reduced pressure. The resulting residue was dissolved in THF (5 mL), and stirred therein at 60° C. for 2 hours after adding 1,1′-carbonyldiimidazole (0.288 g, 1.78 mmol). After cooling the mixture to room temperature, the precipitate was removed by filtration, and the filtrate was collected and concentrated. The resulting residue was dissolved in DMF (5 mL), and stirred therein at room temperature for 1.5 hours after adding methyl iodide (0.100 mL, 1.61 mmol) and potassium carbonate (222 mg, 1.61 mmol). Thereafter, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was collected, washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give (S)-3-methyl-5-[5-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)pyridin-3-yl]-1,3,4-oxadiazol-2(3H)-one (102 mg, 45%).

Provenance & Evidence