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

Participants

Reaction Steps

Following the procedure as described in Example 4, making variations as necessary to replace 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid with 4-methyl-2-(1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)thiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 65% yield: mp 204-205° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.94-8.83 (m, 2H), 8.52 (br s, 1H), 8.43 (br s, 1H), 7.78-7.66 (m, 3H), 7.58-7.51 (m, 2H), 7.38-7.29 (m, 1H), 5.77 (s, 2H), 4.45-4.39 (m, 2H), 2.57 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.5, 157.9, 155.0, 149.3, 148.6, 142.3, 140.6, 135.7, 135.2, 129.3, 129.5, 126.3, 126.2, 125.3, 124.1, 123.9, 53.1, 41.1, 17.5; Ms (ES+) m/z 459.3 (M+1).

Provenance & Evidence