Water → N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

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Reaction Steps

To a solution of N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamide (0.47 g, 0.96 mmol) in tetrahydrofuran (10 mL) was added water (5 mL) and trifluoroacetic acid (5 mL) at ambient temperature. The resulting reaction mixture was heated to reflux for 5 hours. The solvent was removed in vacuo and the residue was purified by column chromatography to afford the title compound in 76% yield (0.32 g): mp 133-134° C.; 1H NMR (300 MHz, CDCl3) δ 7.35-6.97 (m, 9H), 6.10 (t, J=5.7 Hz, 1H), 5.99 (d, J=5.9 Hz, 1H), 5.03 (s, 1H), 4.53 (d, J=5.7 Hz, 2H), 4.41 (s, 2H), 3.60-3.54 (m, 1H), 3.27-3.23 (m, 1H), 2.52 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.4, 162.1, 160.8, 157.0, 153.5, 152.4, 137.9, 131.1, 129.9, 128.7, 127.8, 117.9, 115.9, 115.7, 49.3, 46.6, 44.0, 17.0; MS (ES+) m/z 441.3 (M+1).

Provenance & Evidence