Triethylamine → HCID 21993927, compound

Participants

Reaction Steps

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.58 g, 8.24 mmol) was added to a stirred suspension of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid (900 mg, 4.12 mmol) and N-hydroxysuccinimide (948 mg, 8.24 mmol) in acetonotrile (10 ml) at room temperature and the mixture was stirred at room temperature for 2 hours. A solution of 4-(3-aminopropan-1-yl)-1-(3-phenylpropan-1-yl)-2-oxopiperazine (1.38 g, 5.01 mmol), triethylamine (459 mg, 4.54 mmol) and 1,8-diazabicyclo[5.4.0]undecene (1.25 g, 8.24 mmol) in acetonitrile (20 ml) was added to the mixture. After stirring at room temperature for 1 day, the reaction mixture was concentrated in vacuo. The residue was dissolved in water and extracted with chloroform. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (60 g) with Ethyl acetate-Methanol (5:1) to give N-[3-[1-(3-phenylpropan-1-yl)-2-oxopiperazin-4-yl]propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide as a purple amorphous powder (978 mg, 50%).

Provenance & Evidence