4-Benzyloxy-2(1H)-pyridone → N-Benzyl-5-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylfuran-2-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 3, making variations only as required to use 4-(benzyloxy)pyridin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-5-bromo-3-methylfuran-2-carboxamide in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 22% yield: mp 191-192° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.92 (t, J=6.2 Hz, 1H), 8.23 (d, J=7.9 Hz, 1H), 7.49-7.20 (m, 10H), 6.78 (s, 1H), 6.25 (dd, J=7.9, 2.7 Hz, 1H), 6.06 (d, J=2.7 Hz, 1H), 5.15 (s, 2H), 4.43 (d, J=6.2 Hz, 2H), 2.33 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.4, 160.7, 158.3, 143.7, 139.6, 137.1, 135.4, 134.5, 128.4, 128.3, 128.2, 128.0, 127.2, 126.7, 105.6, 101.8, 97.6, 69.9, 41.5, 11.0; MS (ES+) m/z 415.3 (M+1).

Provenance & Evidence