Imidazole → HCID 68706459, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N,N-dimethylsulfamoyl)imidazole (Preparation described in Winter, J., Retey, J. Synthesis. 1994, 3, 245-246; 47 mg, 0.27 mmol) in 1 mL THF, cooled to −78° C. was added n-butyllithium (2.5 M solution in hexanes, 0.12 mL, 0.29 mmol) dropwise. The reaction was stirred at −78° C. for 15 min and zinc chloride (0.5 M solution in THF, 1.6 mL, 0.81 mmol) was added. After warming to rt over 1 h, 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-bromo-N-methyl-N-(methylsulfonyl)benzenamine (100 mg, 0.18 mmol) and tetrakis(triphenylphosphine)palladium(0) (20.8 mg, 0.018 mmol) were added. The mixture was heated in a microwave oven to 80° C. for 0.75 h, quenched with water and extracted with EtOAc. The combined organic layers were washed with brine. Drying, solvent evaporation and flash chromatography (50-100% EtOAc/hexanes) gave 3-(1-(dimethylsulfamoyl)-1H-imidazol-2-yl)-5-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-N-methyl-N-(methylsulfonyl)benzenamine. 1H NMR (CDCl3) δ 8.26 (m, 1H), 8.15 (m, 1H), 7.87 (m, 1H), 7.49 (d, J=1.6 Hz, 1H), 7.26 (m, 3H), 7.18 (d, J=1.6 Hz, 1H), 7.08 (m, 2H), 3.60 (d, J=12 Hz, 1H), 3.40 (m, 4H), 2.95 (s, 3H), 2.64 (s, 6H), 1.71 (s, 3H), 1.42 (bs, 9H).

Provenance & Evidence