Acetic Acid → HCID 11466590, compound

Participants

Reaction Steps

A solution of 7-methoxy-6-methyl-4-(4-(2-pyrrolidin-1-yl-ethoxy)-benzyl)-3-(4-trifluoromethyl-phenyl)-chromen-2-one (50 mg, 0.093 mmol) in 1:1 48% HBr:AcOH (3 μL) was heated at 130° C. for 7 h. The mixture was cooled to room temperature and poured into AcOEt/1 M NaOH. The layers were separated and the organic phase was washed with H2O (2×) and brine and dried (MgSO4). The solvent was removed in vacuo. The residue was purified using reverse phase HPLC, followed by extraction with AcOEt/NaHCO3 to provide the desired compound as a yellow solid (25 mg, 52%). 1H NMR (300 MHz, CDCl3) δ 7.60 (d, J=8.0 Hz, 2H), 7.32 (d, J=8.0 Hz, 2H), 7.21 (d, J=0.75 Hz, 1H), 6.86 (d, J=8.8 Hz, 2H), 6.72 (s, 1H), 6.62 (d, J=8.8 Hz, 2H), 4.14 (t, J=5.5 Hz, 2H), 3.92 (s, 2H), 3.13 (t, J=5.5 Hz, 2H), 2.97–2.85 (br s, 4H), 2.13 (s, 3H), 2.00–1.89 (m, 4H); MS (ESI) m/z 523.9 (M)+; HPLC tR 5.07 min.

Provenance & Evidence