Dimethylamine → HCID 67236391, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-((5-(2-(4-Chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethyl methanesulfonate (230 mg, 0.36 mmol, 1.0 eq), dimethylamine (7.2 mL, 14.4 mmol, 40.0 eq, 2.0 M in THF) and diisopropylamine (0.2 mL, 1.1 mmol, 3.0 eq) in anhyd DMF (3.5 mL) was heated at 110° C. for 16 h. The mixture was diluted with EtOAc, washed sequentially with brine, satd NaHCO3 and brine, dried over MgSO4 and concentrated to provide 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)-N,N-dimethylethanamine (187 mg). 1H NMR (400 MHz, CDCl3) δ 7.13 (s, 1H), 7.07 (d, J=8.2 Hz, 1H), 6.72-6.65 (m, 2H), 6.48-6.40 (m, 2H), 6.34-6.25 (m, 4H), 3.98-3.92 (m, 4H), 3.68 (s, 3H), 2.68 (t, J=5.5 Hz, 2H), 2.28 (s, 3H), 1.41 (s, 6H); MS (EI) m/z 590 (MH+).

Provenance & Evidence