Reaction #59771

Reaction equation

4′-[5-(Azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide

Intermediate 44

4′-[5-(Azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide

triethylamine

ethyl 2-cyclopropylethanimidate hydrochloride

→

N-cyclopropyl-4′-[5-(cyclopropylmethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe ethanol was removed under vacuum
2. 2
   Washeluted with an ethyl acetate/cyclohexane gradient
3. 3
   OtherEvaporation of the solvent from the product fractions

Procedure

4′-[5-(Azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 44) (40 mg), triethylamine (0.051 ml) and ethyl 2-cyclopropylethanimidate hydrochloride (23 mg) in ethanol (3 ml) were heated at 80° C. for 16 hours. The ethanol was removed under vacuum, the residue applied to a bond-elut (silica) and eluted with an ethyl acetate/cyclohexane gradient. Evaporation of the solvent from the product fractions gave N-cyclopropyl-4′-[5-(cyclopropylmethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide.

Source