Dimethylformamide → 1-(4-Fluorophenyl)-N-methyl-N-((3-methylpyridin-4-yl)methyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide

Participants

Reaction Steps

To a solution of 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylic acid (11) (200 mg, 0.52 mmol) in DMF (5 mL) N-methyl-1-(3-methylpyridin-4-yl)methanamine (86 mg, 0.63 mmol), and triethylamine (159 mg, 1.57 mmol) was added. At room temperature, TBTU (252 mg, 0.785 mmol) was added in one portion and the mixture was stirred at room temperature overnight. The mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over sodium sulfate. The mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (10%-80% ethyl acetate in hexanes) to give 1-(4-fluorophenyl)-N-methyl-N-((3-methylpyridin-4-yl)methyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide (502). 1H NMR (400 MHz, CDCl3) δ: 8.41-8.36 (m, 2H), 7.20-7.17 (m, 2H) 7.12-6.99 (m, 3H), 6.78-6.74 (m, 3H), 4.62 (s, 2H), 4.35 (s, 2H), 3.04 (s, 3H), 2.20 (s, 3H). LC-MS ESI m/z; found 501.1 [M+H]+.

Provenance & Evidence