Ammonium Chloride → HCID 178441995, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ({1-bromo-6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (71 mg, 0.141 mmol), prepared in the previous step, sodium azide (27.8 mg, 0.427 mmol) and ammonium chloride (25 mg, 0.467 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for 3 h. Following the reaction by MS, starting material remained. Additional sodium azide (25 mg, 0.38 mmol) and ammonium chloride (25 mg, 0.467 mmol) were added and the reaction stirred at 100° C. for two more hours. This procedure was repeated four additional times until the MS showed that the reaction went to completion. The reaction was filtered, acidified with 5 mL of 1N HCl and then diluted with 10 mL of H2O. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (52 mg, 67%) as a brown solid, mp 235-237° C. Elemental Analysis for C27H22BrN5O3+0.23 mol H2O Calc'd: C, 59.12; H, 4.07; N, 12.77. Found: C, 59.36; H, 4.27; N, 12.23.

Provenance & Evidence