Reaction #59707

Reaction equation

N-Cyclopropyl-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide

Intermediate 40

N-Cyclopropyl-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide

2-chloro-1,1,1-triethoxyethane

→

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

Conditions

Workup

1. 1
   Washeluted with an ethyl acetate/cyclohexane gradient

Procedure

N-Cyclopropyl-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 40) (150 mg) in 2-chloro-1,1,1-triethoxyethane (5 ml) was heated at 150° C. for 18 hours. The reaction was applied to a biotage cartridge (silica, 90 g) and eluted with an ethyl acetate/cyclohexane gradient. The product fractions were reduced to dryness under vacuum to give 4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide.

Source