Reaction Steps
This was prepared analogously to 2ay. The reaction of 1cx (0.613 g, 1.53 mmol), N-methyl-1,2-diaminoethane (0.672 mL, 7.62 mmol), and triethylamine (213 μL, 1.53 mmol) in 2-methoxyethanol, followed by chromatography on silica with a chloroform/methanol gradient, yielded 2cz as a pure yellow powder (0.380 g, 57%). 1H NMR (CDCl3): δ=8.56 (d, 1H, J=7.7 Hz), 8.44 (d, 1H, J=8.4 Hz), 6.16 (d, 1H, J=8.1 Hz), 7.60 (t, 1H, J=7.8 Hz), 6.67 (d, 1H, J=8.4 Hz), 6.25 (br t, 1H, J=4.2 Hz), 4.58 (t, 1H, J=3.6 Hz), 4.16 (t, 2H, J=7.6 Hz), 3.85 (m, 1H), 3.74 (m, 1H), 3.49 (m, 1H), 3.43 (m, 1H), 3.06 (t, 2H, J=5.7 Hz), 2.52 (s, 3H), 1.78-1.66 (m, 6H), 1.53-1.49 (m, 6H). 13C{1H} NMR: δ=164.9, 164.3, 149.8, 134.7, 131.3, 130.0, 126.5, 124.8, 123.3, 120.6, 110.4, 104.6, 98.9, 67.6, 62.4, 49.7, 42.0, 40.3, 36.1, 30.9, 29.7, 28.3, 25.7, 24.1, 19.8. ESI/MS m/z 440 (M+H)+.
