Ammonium Chloride → HCID 178490051, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-5-((5-(2-(3-chloro-4-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)benzonitrile (104 mg, 0.20 mmol), sodium azide (130 mg, 2.0 mmol, 10.0 eq) and NH4Cl (110 mg, 2.0 mmol) in DMF (2 mL, anhyd) was stirred at 110° C. for 16 h. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The combined extracts were washed with water and brine, then dried over MgSO4 and concentrated. Purification by column chromatography (silica, 0 to 20% MeOH/DCM) provided the title compound (85 mg, 76%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.59 (d, J=1.7 Hz, 1H), 7.47 (d, J=8.3 Hz, 1H), 7.18-7.14 (m, 2H), 6.95-6.89 (m, 3H), 6.78-6.74 (m, 2H), 6.37-6.31 (m, 2H), 4.17 (s, 2H), 3.81 (s, 3H), 1.39 (s, 6H); MS (EI) m/z 569 (MH+).

Provenance & Evidence