Potassium Iodide → N-Cyclopropyl-4'-{5[-(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31479

Reaktionsgleichung

Reaktionsgleichung von HRID 31479
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([NH:23][CH:24]4[CH2:26][CH2:25]4)=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)=[N:5][N:4]=1.[I-].[K+]>C(NCC)C>[CH:24]1([NH:23][C:21]([C:16]2[CH:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]4[O:7][C:3]([CH2:2][N:23]([CH2:24][CH3:25])[CH2:21][CH3:16])=[N:4][N:5]=4)=[CH:9][CH:10]=3)[C:19]([CH3:20])=[CH:18][CH:17]=2)=[O:22])[CH2:26][CH2:25]1

Komponenten

4

Edukt 2

HCID 4875Potassium IodideHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Produkt 1

HCID 10408948N-Cyclopropyl-4'-{5[-(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

4′-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 45) (37 mg) and potassium iodide (5 mg) were mixed in diethylamine (3 ml) and the reaction stirred at room temperature for 18 hours. The excess amine was evaporated under vacuum and the residue purified by bond-elut (silica), eluting with an ethyl acetate/cyclohexane gradient. After evaporation of the solvent this gave N-cyclopropyl-4′-{5-[(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. customThe excess amine was evaporated under vacuum
  2. customthe residue purified by bond-elut (silica)
  3. washeluting with an ethyl acetate/cyclohexane gradient
  4. customAfter evaporation of the solvent this gave N-cyclopropyl-4′-{5-[(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide

Quellen und Nachweise

ORD-Eintrag
ord-7660b4ebd735463abd0da9204de9da53
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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