Triethylamine → HCID 86629190, compound

Participants

Reaction Steps

8-Ethynyl-6-phenyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid (82 mg, 0.251 mmol) was dissolved in DMF (6 ml) and then N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (48 mg, 0.251 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (33.8 mg, 0.251 mmol), and triethylamine (70 μL, 0.501 mmol) were added. The solution was stirred for 15 min and then ethylamine hydrochloride (20.4 mg, 0.251 mmol) was added. The solution was stirred at room temperature for 3 days. The DMF was removed in vacuo. The residue was dissolved in ethyl acetate and extracted with water twice, then dried with brine. The ethyl acetate layer was then condensed with a stream of nitrogen, and dried in vacuo. The residue was dissolved in methylene chloride, and applied to a silica gel column. The product was eluted with ethyl acetate. The product fractions were concentrated in vacuo. The oily residue was dissolved in acetonitrile and several drops of concentrated HCl were added to give the HCl salt. The acetonitrile was removed in vacuo and the HCl salt was dried under high vacuum to give a yellow powder (75 mg, 77%).

Provenance & Evidence