Sodium Azide → 4'-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide

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A solution of sodium azide (40 mg) in water (3.5 ml) was added to (4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 34) (200 mg) in DMF (1.5 ml) and ethanol (7 ml) and the reaction mixture stirred for 5 hours at 90° C. The reaction was concentrated under vacuum and the residue partitioned between water (15 ml) and chloroform (15 ml) and the aqueous extracted with chloroform (2×15 ml). The combined organic extracts were dried (magnesium sulphate), and the solvent evaporated under vacuum to give 4′-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide.

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