3-Pyridinemethanamine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine in place of benzylamine, the title compound was obtained as a white powder in 33% yield: mp 177-179° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.50 (d, J=3.9 Hz, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.29-7.21 (m, 3H), 7.04-6.97 (m, 2H), 6.26 (t, J=5.7 Hz, 1H), 4.57 (d, J 5.7 Hz, 2H), 4.42 (s, 2H), 4.04 (t, J=8.1 Hz, 2H), 3.43 (t, J=8.1 Hz, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 164.1, 162.6, 160.8, 157.3, 155.3, 153.6, 148.5, 136.0, 134.1, 131.3, 129.9, 123.7, 116.9, 115.9, 115.6, 47.2, 42.0, 41.6, 41.3, 17.2; MS (ES+) m/z 475.0 (M+1).

Provenance & Evidence