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

HRID 31470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31470
[N:1]([CH2:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([CH3:22])=[C:20]([F:23])[CH:19]=[C:18]([C:24]([NH:26][CH:27]4[CH2:29][CH2:28]4)=[O:25])[CH:17]=3)=[CH:12][CH:11]=2)=[N:7][N:6]=1)=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:1][CH2:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([C:16]3[C:21]([CH3:22])=[C:20]([F:23])[CH:19]=[C:18]([C:24]([NH:26][CH:27]4[CH2:29][CH2:28]4)=[O:25])[CH:17]=3)=[CH:14][CH:15]=2)=[N:7][N:6]=1

Komponenten

5

Edukt 2

HCID 866046944'-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide2×HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 104289704'-[5-(aminomethyl)-1,3,4oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

4′-[5-(Azidomethyl)-1,3,4oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 35) (208 mg) and palladium on carbon (10% w/w, 21 mg) in ethanol (10 ml) were hydrogenated under 1 Atm. of hydrogen for 24 hours at room temperature. The reaction was filtered through celite and the filtrate reduced to dryness under vacuum. The residue was applied to a bond-elut (silica, 10 g) and eluted with an ethyl acetate/cyclohexane gradient (50-100% ethyl acetate) and then with methanol in ethyl acetate (0-50%). The solvent was evaporated from the product fractions under vacuum to give 4′-[5-(aminomethyl)-1,3,4oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. filtrationThe reaction was filtered through celite
  2. washeluted with an ethyl acetate/cyclohexane gradient (50-100% ethyl acetate)
  3. customThe solvent was evaporated from the product fractions under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-870d090c839f4084ba12bc205d750396
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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