1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67351305, compound

Participants

Reaction Steps

(S)-2-{5-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-2-oxo-1,3,4-oxadiazol-3(2H)-yl}acetic acid (229 mg, 0.49 mmol) obtained in Step 2 was suspended in dichloromethane (5 mL), and the mixture was stirred at room temperature for 2 hours after adding 1-hydroxybenzotriazole (133 mg, 0.98 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (188 mg, 0.98 mmol), and a 2.0 mol/L dimethylamine/THF solution (2.45 mL, 4.88 mmol). After diluting the mixture with chloroform, the organic layer was washed with water and 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)—N,N-dimethyl 2-{5-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-2-oxo-1,3,4-oxadiazol-3(2H)-yl}acetamide (142 mg, 58%).

Provenance & Evidence