Ammonium Chloride → HCID 59825732, compound

Participants

Reaction Steps

To a solution of 60 mg (0.126 mmol) of 9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-6.6 dimethyl-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid in 2 ml dimethylformamide was added successively 72 mg (0.189 mmol) of HBTU, 14 mg (0.253 mmol) of ammonium chloride, 74 mg (0.574 mmol) of N,N-diisopropylethylamine in a round bottom flask. The reaction mixture was stirred overnight at room temperature. Water was then added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried on magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The residue was purified by preparative LCMS (method C) giving 8.9 mg of 9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxamide (12% yield). Analytical LC/MS method B: [M+H]+=474.5; retention time: 2.90 min; 70% UV (DAD) purity.

Provenance & Evidence