1,1'-Carbonyldiimidazole → 2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Participants

Reaction Steps

To a solution of 2-amino-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.50 g, 2.01 mmol) in tetrahydrofuran (30 mL) was added 1,1′-carbonyldiimidazole (0.39 g, 2.41 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 6 hours and N-(4-fluorophenethyl)-2,2-dimethoxyethanamine (0.59 g, 2.61 mmol) was added. The reaction mixture was stired for 17 hour at ambient temperature. The solvent was removed in vacuo, and the residue was purified by column chromatography eluted with dichloromethane/methanol (4/1) to afford 2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide as an oil in 19% yield (0.19 g): MS (ES+) m/z 502.4 (M+1).

Provenance & Evidence