Reaction Steps
From acid 18t, with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a bright yellow solid (75%), mp 183-184° C., (from acetonitrile). 1H NMR (CDCl3): δ 2.25 [s, 6H, N(CH3)2], 2.57 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.67 (s, 3H, ArCH3), 3.66 (q, J=6.1 Hz, CH2, CH2CH2NMe2), 5.30 (s, 2H, CH2Pyr), 7.10 (dd, J=7.0, 5.2 Hz, 1H, H-5′), 7.26-7.33 (m, 2H, H-3′, H-8), 7.52-7.59 (m, 2H, H-4′, H-7), 7.64 (d, J=8.2 Hz, 1H, H-9), 8.46 (d, J=4.4 Hz, 1H, H-6′), 8.66 (s, 1H, H-3), 9.02 (s, 1H, H-10), 10.79 (br t, J=5.1 Hz, 1H, CONH). 13C NMR (CDCl3): δ 18.3 (ArCH3), 37.3 (CH2CH2NMe2), 45.2 [N(CH3)2], 53.7 (CH2Pyr), 58.6 (CH2CH2NMe2), 109.6 (C-4), 119.1 (C-10a), 122.1 (CH, C-3′), 122.7 (CH, C-5′), 125.5 (C-9a), 126.4 (CH, C-8), 127.0 (CH, C-9), 132.6 (CH, C-7), 135.6 (C-6), 136.7 (CH, C-4′), 139.6 (CH, C-10), 143.4 (CH, C-3), 147.7 (C-5a), 148.5 (C-4a), 149.6 (CH, C-6′), 155.0 (C-2′), 162.2 (C-1), 164.3 (CONH).
