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

HRID 31428

Reaktionsgleichung

Reaktionsgleichung von HRID 31428
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]([C:25]([NH:27][CH:28]4[CH2:30][CH2:29]4)=[O:26])[CH:19]=3)=[CH:14][CH:13]=2)=[N:9][N:8]=1>O.CN(C=O)C.C(O)C>[N:1]([CH2:6][C:7]1[O:11][C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]([C:25]([NH:27][CH:28]4[CH2:29][CH2:30]4)=[O:26])[CH:19]=3)=[CH:16][CH:17]=2)=[N:9][N:8]=1)=[N+:2]=[N-:3]

Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Produkt 1

HCID 866046954'-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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,

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. customThe solvents were evaporated under vacuum
  4. customthe residue partitioned between water (20 ml) and chloroform (15 ml)
  5. extractionThe aqueous was extracted with chloroform (15 ml)
  6. dry with materialthe combined organic phases dried (sodium sulphate)

Quellen und Nachweise

ORD-Eintrag
ord-9de561ba42d14a5fa7eb2db4be4768e4
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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