3-Pyridinemethanamine → 4-methyl-2-(5-oxo-1-(4,4,4-trifluorobutyl)-1H-1,2,4-triazol-4(5H)-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as described in Example 21, making variations as required to replace 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acid with 4-methyl-2-(5-oxo-1-(4,4,4-trifluorobutyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 35% yield: mp 184-185° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.57 (br s, 1H), 8.49 (br s, 1H), 8.27 (s, 1H), 7.75-7.63 (m, 1H), 7.32-7.20 (m, 1H), 6.62 (t, J=5.6 Hz, 1H), 4.59 (d, J=5.6 Hz, 2H), 3.91 (t, J=6.5 Hz, 2H), 2.63 (s, 3H), 2.28-1.96 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 161.7, 153.4, 150.9, 150.0, 149.2, 149.1, 135.8, 131.0, 128.5, 124.8, 121.2, 44.5, 41.2, 31.3, 30.9, 21.3, 17.2; MS (ES+) m/z 427.3 (M+1).

Provenance & Evidence