Reaktion #59706

Reaktionsgleichung

sodium azide

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

Intermediate 45

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

→

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

Lösungsmittel

water

DMF

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturat reflux for 2 hours
3. 3
   SonstigeThe solvents were evaporated under vacuum
4. 4
   Sonstigethe residue partitioned between water (20 ml) and chloroform (15 ml)
5. 5
   ExtraktionThe aqueous was extracted with chloroform (15 ml)
6. 6
   Trocknenthe combined organic phases dried (sodium sulphate)

Vorschrift

A solution of sodium azide (14.8 mg) in water (1.25 ml) was added to 4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 45) (40 mg) in DMF (0.5 ml) and ethanol (2.5 ml) and the mixture heated at reflux for 2 hours. The solvents were evaporated under vacuum and the residue partitioned between water (20 ml) and chloroform (15 ml). The aqueous was extracted with chloroform (15 ml) and the combined organic phases dried (sodium sulphate) and reduced to dryness in vacuo to give 4′-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide,

Quelle