Water → HCID 71117345, compound

Participants

Reaction Steps

To a solution of N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide (508) (70 mg, 0.143 mmol) in DMF (1.5 mL) was added sodium hydride (60% in mineral oil, 7 mg, 0.172 mmol) and the reaction was stirred for 15 minutes. Iodoethane (13 mL, 0.172 mmol) was added and stirred for 1 hour. Water was added slowly and the reaction was extracted with 1:1 EtOAc:Hexane, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (90-100% EtOAc in hexanes) to afford N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-N-ethyl-1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide (519). 1H NMR (400 MHz, CDCl3) δ: 7.33 (s, 1H), 7.18-6.91 (m, 6H), 6.82-6.73 (m, 1H), 4.37 (s, 2H), 4.34 (s, 2H), 3.77 (s, 3H), 3.37 (q, J=7.0, 2H), 2.16-2.06 (m, 3H), 1.25-1.00 (m, 3H). LC-MS ESI m/z; found 518.0 [M+H]+.

Provenance & Evidence