Reaction #59701

Reaction equation

N-Cyclopropyl-5-fluoro-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide

Intermediate 29

N-Cyclopropyl-5-fluoro-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-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide

Conditions

Workup

1. 1
   OtherThe reaction was absorbed onto silica
2. 2
   Otherpurified by chromatography on a biotage column (silica, 40 g)
3. 3
   Washeluting with cyclohexane

Procedure

N-Cyclopropyl-5-fluoro-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 29) (580 mg) in 2-chloro-1,1,1-triethoxyethane (2.5 ml) was heated at 80° C. for 20 hours. The reaction was absorbed onto silica and purified by chromatography on a biotage column (silica, 40 g), eluting with cyclohexane and then with ethyl acetate/cyclohexane (2:3). The product fractions were reduced to dryness under vacuum to give 4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide.

Source