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

HRID 31429

Reaktionsgleichung

Reaktionsgleichung von HRID 31429
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][NH2:23])=[O:21])=[CH:16][CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[Cl:24][CH2:25][C:26](OCC)(OCC)OCC>>[Cl:24][CH2:25][C:26]1[O:21][C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:9]3[C:10]([CH3:13])=[CH:11][CH:12]=[C:7]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:6])[CH:8]=3)=[CH:15][CH:16]=2)=[N:22][N:23]=1

Komponenten

3

Edukt 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 11438287N-cyclopropyl-4'-(hydrazinocarbonyl)-6-methyl-1,1'-biphenyl-3-carboxamide2×

Produkt 1

HCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Versuchsvorschrift

N-Cyclopropyl-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 40) (150 mg) in 2-chloro-1,1,1-triethoxyethane (5 ml) was heated at 150° C. for 18 hours. The reaction was applied to a biotage cartridge (silica, 90 g) and eluted with an ethyl acetate/cyclohexane gradient. The product fractions were reduced to dryness under vacuum to give 4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. washeluted with an ethyl acetate/cyclohexane gradient

Quellen und Nachweise

ORD-Eintrag
ord-f789bfc92c094fa08e0dba0cc7255c53
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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