Potassium Carbonate → 2-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 1524212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524212
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16](=[O:19])[NH:17][N:18]=3)[CH:15]=2)=[CH:6][CH:5]=1.Cl[CH2:23][C:24]1[O:28][N:27]=[C:26]([CH3:29])[N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH3:29][C:26]1[N:25]=[C:24]([CH2:23][N:17]2[C:16](=[O:19])[N:14]3[CH:15]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=4)[CH:11]=[CH:12][C:13]3=[N:18]2)[O:28][N:27]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 127748255-(Chloromethyl)-3-methyl-1,2,4-oxadiazoleHCID 58044589HCID 58044589, Verbindung

Produkt 1

HCID 565958832-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 90 mg 6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (0.30 mmol), 40 mg 5-(chloromethyl)-3-methyl-1,2,4-oxadiazole (0.30 mmol) and 23 mg potassium carbonate (0.17 mmol) in 2 mL DMA was heated at 110° C. for 2 h. The reaction mixture was then filtered and the filtrate concentrated. The residue was column purified on 12 g silica, eluting with 36 mL 5% ethyl acetate in hexanes, then 5-50% over 60 mL, and then 50% 120 mL. 2-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one was isolated as a yellow solid. m/z (ESI)=392.0 [M+H]+. 1H NMR (δ, d6-DMSO, 400 MHz) 7.95 (dd, 1H) 7.54 (d, 2H), 7.40 (dd, 1H), 7.32 (d, 2H), 7.20 (dd, 1H) 5.43 (s, 2H), 2.40 (s, 3H)

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated
  3. custompurified on 12 g silica
  4. washeluting with 36 mL 5% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0e5b875dfd934e85837fd4299bf2be41
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079901B2

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