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

HRID 31423

Reaktionsgleichung

Reaktionsgleichung von HRID 31423
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([NH:23][NH2:24])=[O:22])=[CH:17][CH:16]=3)[C:10]([CH3:14])=[C:11]([F:13])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[Cl:25][CH2:26][C:27](OCC)(OCC)OCC>>[Cl:25][CH2:26][C:27]1[O:22][C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:9]3[C:10]([CH3:14])=[C:11]([F:13])[CH:12]=[C:7]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:6])[CH:8]=3)=[CH:16][CH:17]=2)=[N:23][N:24]=1

Komponenten

3

Edukt 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 69318167N-cyclopropyl-5-fluoro-4'-(hydrazinocarbonyl)-6-methyl-1,1'-biphenyl-3-carboxamide2×

Produkt 1

HCID 693149174'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide

Versuchsvorschrift

N-Cyclopropyl-5-fluoro-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 29) (580 mg) in 2-chloro-1,1,1-triethoxyethane (2.5 ml) was heated at 80° C. for 20 hours. The reaction was absorbed onto silica and purified by chromatography on a biotage column (silica, 40 g), eluting with cyclohexane and then with ethyl acetate/cyclohexane (2:3). The product fractions were reduced to dryness under vacuum to give 4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide.

Aufarbeitung

  1. customThe reaction was absorbed onto silica
  2. custompurified by chromatography on a biotage column (silica, 40 g)
  3. washeluting with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-3a873200c5d94c059eef46c74691d807
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425555B2

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