3-Pyridinemethanamine → 2-(1-(2-cyclopropylethyl)-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-(2-cyclopropylethyl)-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 19% yield: mp 124-125° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.52 (s, 1H), 8.09 (s, 1H), 7.33-7.22 (m, 2H), 6.33 (t, J=5.7 Hz, 1H), 4.62 (d, J=5.7 Hz, 2H), 4.48 (t, J=7.0 Hz, 2H), 2.71 (s, 3H), 1.82 (q, J=7.0 Hz, 2H), 0.71-0.56 (m, 1H), 0.52-0.43 (m, 2H), 0.08-0.01 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 161.9, 158.3, 157.3, 149.3, 149.1, 142.4, 135.7, 133.6, 124.1, 123.7, 121.8, 51.1, 41.6, 35.1, 17.4, 8.1, 4.3; MS (ES+) m/z 369.3 (M+1).

Provenance & Evidence