1,4-Dioxane → HCID 44554596, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 133 compound (60 mg, 0.119 mmol), methylpyrazole boronic acid (29.7 mg, 0.143 mmol), Pd(PPh3)4 (13.7 mg, 0.012 mmol), K3PO4 (50.5 mg, 0.238 mmol, aq) in dioxane (2 ml) was vacuumed and purged to N2 for 3 times, then reaction mixture was heated at 110° C. for 3 hrs. Reaction mixture was diluted with EtOAc, washed with brine dried and concentrated. Separated by prep TLC (hex:EtOAc:CH3OH=6:5:1) to give 4-{5-[(4-chlorophenyl)sulfanyl]-1-methyl-4-[4-(methylsulfonyl)phenyl]-1H-imidazol-2-yl}-1-methyl-1H-pyrazole (25 mg) 1H NMR (500 MHz), [(CDCl3]: 8.35 (m, 1H), 7.95 (m, 3H), 7.25 (m, 3H), 7.01 (m, 2H), 4.10 (s, 3H), 3.78 (s, 3H), 3.10 (s, 3H). LCMS: [M+1]+=459.0. Human FAAH lysate assay: IC50=13.9 nM.

Provenance & Evidence