Water → HCID 135465356, Verbindung

HRID 271444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271444
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12](N3C=CN=C3)[N:11]3[C:19](=[O:22])[NH:20][N:21]=[C:10]3[C:9]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]([F:47])([F:46])[F:45])=[N:42][CH:43]=1.[OH2:48]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:48])[N:11]3[C:19](=[O:22])[N:20]([CH2:37][C:38]4[CH:43]=[N:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=4)[N:21]=[C:10]3[C:9]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 58772834HCID 58772834, Verbindung

Produkt 1

HCID 135465356HCID 135465356, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 7,8-bis(4-chlorophenyl)-5-(1H-imidazol-1-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (60 mg, 0.14 mmol) in DMF (0.5 mL) at room temperature under argon was added K2CO3 (25 mg, 0.18 mmol), followed by 5-(chloromethyl)-2-(trifluoromethyl)pyridine (28 mg, 0.14 mmol). The reaction mixture was stirred at 50° C. in a pre-heated oil bath for 30 min. After the reaction mixture was cooled to room temperature, water (5 mL) and EtOAc (5 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product thus obtained was purified by preparative reverse phase HPLC (without TFA) to obtain 22.5 mg of the title compound as a white solid. HPLC/MS: retention time=3.871 min, [M+H]30 =532.

Aufarbeitung

  1. temperatureAfter the 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
  6. customThe crude product thus obtained
  7. customwas purified by preparative reverse phase HPLC (without TFA)

Quellen und Nachweise

ORD-Eintrag
ord-7b61fecdf9674a12a63e8b0ee5144f80
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

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