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

HRID 31482

Reaktionsgleichung

Reaktionsgleichung von HRID 31482
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[N:30]([CH:32]=O)C>C1(N)CCCCC1>[CH:32]1([NH:30][CH2:2][C:3]2[O:7][C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]4[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([NH:23][CH:24]5[CH2:26][CH2:25]5)=[O:22])[CH:15]=4)=[CH:10][CH:9]=3)=[N:5][N:4]=2)[CH2:12][CH2:13][CH2:8][CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Produkt 1

HCID 102521294'-{5-[(Cyclohexylamino)methyl]-1,3,4-oxadiazol-2-yl}-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7965CyclohexylamineLösungsmittel

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 cyclohexylamine (2 ml) and DMF (2 ml) and the reaction stirred at room temperature for 18 hours. The solvents were 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 4′-{5-[(cyclohexylamino)methyl]-1,3,4-oxadiazol-2-yl}-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. customThe solvents were 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 4′-{5-[(cyclohexylamino)methyl]-1,3,4-oxadiazol-2-yl}-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide

Quellen und Nachweise

ORD-Eintrag
ord-21f57a3f9b32472986eedf07d12ae035
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

Verknüpfte Notizen

Wird geladen…