Reaction Steps
Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with 3,4-difluorobenzylamine to react with (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as an off-white solid in 74% yield: mp 62-65° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 8.54 (t, J=5.9 Hz, 1H), 7.44-7.30 (m, 4H), 7.21-7.12 (m, 3H), 4.60 (d, J=15.6 Hz, 1H), 4.35 (d, J=5.9 Hz, 2H), 4.30 (d, J=15.6 Hz, 1H), 4.19 (dd, J=10.0, 9.1 Hz, 1H), 3.80-3.69 (m, 1H), 3.55 (dd, J=10.0, 6.2 Hz, 1H), 2.47 (s, 3H), 1.22 (d, J=6.2 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.8, 161.5 (d, 1JC-F=244 Hz), 157.2, 154.9, 151.3, 150.4 (dd, JC-F=66, 13 Hz), 147.1 (dd, JC-F=66, 13 Hz), 137.6 (dd, JC-F=5, 4 Hz), 133.1 (d, 4JC-F=3 Hz), 130.0 (d, 3JC-F=8 Hz), 124.0 (dd, JC-F=7, 3 Hz), 117.6, 117.3 (d, JC-F=17 Hz), 116.3 (d, JC-F=17 Hz), 115.4 (d, 2JC-F=21 Hz), 49.4, 48.6, 43.7, 41.7, 18.4, 17.1; MS (ES+) m/z 474.8 (M+1).
