Phthalic Anhydride → HCID 86710422, compound

Participants

Reaction Steps

To a solution of (S)-8-((2-amino-4-methylpentyl)oxy)-9-iodo-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (130 mg, 0.140 mmol) in 1,4-dioxane (3 mL) was added N-ethyl-N-isopropylpropan-2-amine (54.2 mg, 0.419 mmol) and isobenzofuran-1,3-dione (24.83 mg, 0.168 mmol). The reaction mixture was refluxed for 16 h. After cooling, the reaction mixture was diluted with EtOAc (10 mL). The organics were washed with water, saturated aqueous NaHCO3. The combined aqueous layers were extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC plate using 2% Methanol: DCM as a eluent system to afford (S)-2-(1-((9-iodo-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione (85 mg, 0.084 mmol, 60% yield) as a pale yellow solid. LC/MS (ESI) m/e 596.5 [(M+H)+, calcd for C28H27IN3O4 596.1] LC/MS retention time (method E): tR=1.3 min.

Provenance & Evidence