3-Pyridinemethanamine → 2-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)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 2-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 57% yield: mp 140-141° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.73-8.48 (m, 2H), 8.24 (s, 1H), 7.76-7.66 (m, 1H), 7.39-7.19 (m, 1H), 6.71 (br s, 1H), 4.62 (d, J=5.3 Hz, 2H), 4.26 (d, J=7.2 Hz, 2H), 2.72 (s, 3H), 1.39-1.23 (m, 1H), 0.81-0.66 (m, 2H), 0.53-0.38 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 161.9, 158.3, 157.3, 149.2, 148.9, 143.9, 142.5, 135.8, 133.8, 124.1, 121.2, 55.5, 41.6, 17.3, 10.8, 4.4; MS (ES+) m/z 355.3 (M+1).

Provenance & Evidence