1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67348898, compound

Participants

Reaction Conditions

Reaction Steps

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid (180 mg, 0.49 mmol) obtained in Step 1 of Example 56 was suspended in DMF (3.0 mL), and the mixture was stirred at 100° C. for 6 hours after adding 1-hydroxybenzotriazole (200 mg, 1.46 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (280 mg, 1.46 mmol), and N-hydroxyacetamidine (108 mg, 1.46 mmol). Thereafter, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)-5-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (183 mg, 91%).

Provenance & Evidence