(5-Fluoropyridin-3-yl)methanamine → 4-methyl-N-((6-methylpyrazin-2-yl)methyl)-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxamide

Participants

Reaction Steps

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with (6-methylpyrazin-2-yl)methanamine to react with 4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylic acid in place of 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 34% yield: mp 123-123° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.51 (s, 1H), 8.39 (s, 1H), 6.75-6.72 (m, 1H), 4.70 (d, J=4.9 Hz, 2H), 4.17-4.12 (m, 2H), 3.64-3.59 (m, 2H), 3.44-3.39 (m, 2H), 2.63 (s, 3H), 2.57 (s, 3H), 2.25-2.09 (m, 2H), 1.92-1.82 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.5, 157.4, 155.6, 152.9, 152.6, 148.7, 143.4, 142.7, 128.6, 124.9, 117.6, 42.9, 42.3, 42.0, 31.4, 30.9, 21.2, 20.2, 20.1, 17.3; MS (ES+) m/z 442.7 (M+1).

Provenance & Evidence