Synthesis and Characterization of Hexanoyl-Substituted Compound

To a solution of 27 (50 mg, 0.18 mmol) in anhydrous THF, were added triethylamine (26 mg, 0.19 mmol) and hexanoyl chloride. The reaction mixture was stirred at room temperature for 6 hours. The solvent was then removed under vacuum, and the residue was dissolved in ethyl acetate and washed with water. The ethyl acetate fraction was dried using Na₂SO₄ and evaporated under vacuum to obtain the intermediate amide compound. This was dissolved in 0.1 ml of 2M solution of ammonia in MeOH. The sealed reaction vessel was heated in microwave at 150 °C for 1 hour. The solvent was then removed under vacuum and the residue was purified using column chromatography (7% MeOH/dichloromethane) to obtain the compound 32 (8 mg; unoptimized yields). ¹H NMR (500 MHz, CDCl₃) δ 7.81 (d, J = 8.3 Hz, 1H), 7.72 (dd, J = 8.3, 1.0 Hz, 1H), 7.44 (qd, J = 7.0, 3.5 Hz, 1H), 7.38 – 7.29 (m, 3H), 7.18 – 7.10 (m, 1H), 7.06 (d, J = 6.9 Hz, 2H), 5.74 (s, 2H), 5.60 (s, 2H), 2.95 – 2.79 (m, 2H), 1.80 (dt, J = 15.6, 7.6 Hz, 2H), 1.42 – 1.27 (m, 4H), 0.87 (t, J = 7.2 Hz, 3H). ¹³C NMR (126 MHz, CDCl₃) δ 153.50, 150.28, 134.61, 133.41, 128.61, 127.40, 126.51, 125.94, 125.85, 124.85, 121.69, 119.07, 114.42, 48.20, 30.85, 26.97, 26.77, 21.65, 13.23. MS (ESI) calculated for C₂₂H₂₄N₄, m/z 344.20, found 345.21 (M + H)⁺. 2D ¹H COSY and NOESY experiments (included in Supporting Information) provided unambiguous assignment of ¹H resonances.