Hydrochloric Acid → HCID 178488854, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.18 g (0.33 mmol) 4-{2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-3,5-dimethyl-benzonitrile in 3 ml o-xylene were added 0.227 g (1.65 mmol) triethylamine hydrochloride and 0.107 g (2.65 mMol) sodium azide and the solution was heated for 7 h at 145° C. (oil bath temperature). The reaction was allowed to cool down to room temperature overnight and then was poured onto 1M aqueous hydrochloric acid solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The remaining oil was dissolved in acetonitrile, the solution was completely evaporated and the residue dissolved in 20 ml tert-butyl methyl ether under warming to 45° C. The solution was partially evaporated, then stored at 4° C. overnight. The resulting suspension was filtered, washed with tert-butyl methyl ether and dried under high vacuum. Light brown solid (75%). MS (Turbo Spray): m/z=590.44 [M+H].

Provenance & Evidence