1H-1,2,4-Triazole → (5-Methanesulfonyl-2-[1,2,4]triazol-1-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 32768

Reaktionsgleichung

Reaktionsgleichung von HRID 32768
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].[NH:30]1[CH:34]=[N:33][CH:32]=[N:31]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@H]1[C@H](NC)CCCC1>[Cu]I.CN(C=O)C>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[C:3]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Komponenten

7

Edukt 4

HCID 92571H-1,2,4-TriazoleHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 59793691(2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Produkt 1

HCID 68838801(5-Methanesulfonyl-2-[1,2,4]triazol-1-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanoneAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a tube were added successively (2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (compound CK, 0.1 g, 0.19 mmol), 1,2,4-triazole (11 mg, 0.155 mmol), potassium phosphate (71 mg, 0.326 mmol), CuI (7 mg, 0.037 mmol), (1R,2R)-diaminomethylcyclohexane (2.3 mg, 0.015 mmol) and DMF (1 ml). The mixture was heated under argon at 120° C. for 24 hours. The reaction mixture was cooled to room temperature and quenched with water/dichloromethane. The aqueous layer was extracted twice with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: heptane/ethylacetate: 0-100% to provide the title compound as a light grey solid (5 mg, 6%), MS (m/e): 480.4 (M+H, 100%)

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water/dichloromethane
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe crude oil was chromatographed over silicagel

Quellen und Nachweise

ORD-Eintrag
ord-95f81d0e77d14d0099b96b00ce253733
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427612B2

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