2,5-difluoro-N'-hydroxybenzenecarboximidamide → 5-[1-(2-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-yl]-3-(2,5-difluorophenyl)-1,2,4-oxadiazole

HRID 219575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219575
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[N:10]=[N:9]1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[C:25](=[N:27]O)[NH2:26]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH3:13])=[C:11]([C:14]2[O:16][N:26]=[C:25]([C:19]3[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=3[F:17])[N:27]=2)[N:10]=[N:9]1

Komponenten

3

Edukt 2

HCID 43581602,5-difluoro-N'-hydroxybenzenecarboximidamideHCID 153995471-(2-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Produkt 1

HCID 596040655-[1-(2-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-yl]-3-(2,5-difluorophenyl)-1,2,4-oxadiazole

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The title compound was prepared following procedure described for Example 1, but starting from 1-(2-bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid, prepared according to Zhang, Z.-Y. et al. Magn. Reson. Chem. 1998, 36, 159-460 (56.42 mg; 0.20 mmol) and 2,5-difluoro-N′-hydroxybenzenecarboximid amide (JRD-Fluoro, 37.87 mg; 0.22 mmol). The reaction mixture was filtered through an NH2 SPE column (1 g) and evaporated. The residue was taken up into pyridine and heated at 100° C. for 7 h, in order to complete oxadiazole formation. Pyridine was evaporated and the crude product was purified by flash chromatography (SiO2: 10 g; cyclohexane/EtOAc gradient from 90/10 till 50/50) and dried to afford Example 3 as a yellow solid. 1H NMR: (DMSO-d6, 300 MHz) δ 8.06 (dd, J=1.70 Hz, J=7.73 Hz, 1H), 8.02-7.97 (m, 1H), 7.86 (dd, J=1.89 Hz, J=7.53 Hz, 1H), 7.80-7.69 (m, 2H), 7.63 (dt, J=1.91 Hz, J=6.58 Hz, 2H), 2.61 (s, 3H). LC/MS: 419.93 (M+H)+. HPLC (Method A) Rt 4.92 min (Purity: 96%).

Aufarbeitung

  1. customprepared
  2. filtrationThe reaction mixture was filtered through an NH2 SPE column (1 g)
  3. customevaporated
  4. customPyridine was evaporated
  5. customthe crude product was purified by flash chromatography (SiO2: 10 g; cyclohexane/EtOAc gradient from 90/10 till 50/50)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fd7bcae8767b4dadb5957fe2eb68b033
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202856B2

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