3-Pyridinemethanamine → 2-(3-(cyclopropylmethyl)-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-(cyclopropylmethyl)-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 157-158° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.53-8.47 (m, 2H), 8.42-8.40 (m, 1H), 7.68-7.64 (m, 1H), 7.33-7.29 (m, 1H), 4.34 (d, J=5.7 Hz, 2H), 3.99 (t, J=7.2 Hz, 2H), 3.61 (t, J=7.2 Hz, 2H), 3.05 (d, J=6.9 Hz, 2H), 2.43 (s, 3H), 1.03-0.88 (m, 1H), 0.53-0.37 (m, 2H), 0.25-0.12 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 162.3, 157.9, 155.2, 151.7, 149.3, 148.5, 135.6, 135.5, 123.9, 117.7, 48.2, 42.5, 42.3, 41.5, 17.6, 9.3, 3.6; MS (ES+) m/z 372.3 (M+1).

Provenance & Evidence