2-(Bromomethyl)tetrahydro-2H-pyran → N-Benzyl-4-methyl-2-(2-oxo-4-((tetrahydro-2H-pyran-2-yl)methoxy)pyridin-1(2H)-yl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 21, making variation only as required to use 2-(bromomethyl)tetrahydro-2H-pyran in place of 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole to react with N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 66% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.77 (t, J=5.9 Hz, 1H), 8.58 (d, J=8.1 Hz, 1H), 7.36-7.26 (m, 4H), 7.23-7.18 (m, 1H), 6.34 (dd, J=8.1, 2.7 Hz, 1H), 6.11 (d, J=2.6 Hz, 1H), 4.38 (d, J=5.9 Hz, 2H), 4.03-3.94 (m, 2H), 3.86-3.82 (m, 1H), 3.62-3.55 (m, 1H), 3.38-3.31 (m, 1H), 2.53 (s, 3H), 1.76-1.69 (m, 1H), 1.59-1.20 (m, 5H); MS (ES+) m/z 440.2 (M+1).

Provenance & Evidence