Water → 6-((8-bromo-7-(4-chlorophenyl)-5-methyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrile

HRID 2101383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101383
[Br:1][C:2]1[C:3]2[N:4]([C:16](=[O:19])[NH:17][N:18]=2)[C:5]([CH3:15])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][N:29]=1.O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]2[N:4]([C:16](=[O:19])[N:17]([CH2:27][C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][N:29]=3)[N:18]=2)[C:5]([CH3:15])=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 149805356-(Chloromethyl)pyridine-3-carbonitrileHCID 577994038-bromo-7-(4-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Produkt 1

HCID 577993886-((8-bromo-7-(4-chlorophenyl)-5-methyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrileAusbeute 110 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirring solution of 8-bromo-7-(4-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (40 mg, 0.11 mmol) in DMF (0.25 mL) at room temperature under argon was added K2CO3 (50 mg, 0.36 mmol), followed by 6-(chloromethyl)nicotinonitrile (20 mg, 0.13 mmol). The reaction mixture was stirred at 70° C. for 1 h. The reaction mixture was cooled to room temperature, water (2 mL) and EtOAc (5 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure to obtain 55 mg of the title compound as a yellow solid. HPLC/MS: retention time=3.55 min, [M+H]+=454.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe layers were separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5a6935caa9fc4ba48765690beb24e93f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572808B2

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