Ethylenediamine → 4-Fluoro-N-[5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyrazin-2-yl]-benzamide

HRID 1915033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915033
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]([F:22])([F:21])[F:20])=[N:6][CH:7]=1.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(N)CN>O1CCOCC1.[Cu]I.CCOC(C)=O>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:30][C:2]2[CH:7]=[N:6][C:5]([N:8]3[C:12]4[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=4[N:10]=[C:9]3[C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=2)=[O:29])=[CH:26][CH:25]=1

Komponenten

8

Edukt 4

HCID 3301EthylenediamineHCID 62657Potassium Phosphate, TribasicHCID 715724-FluorobenzamideHCID 573569041-(5-Bromopyrazin-2-YL)-2-(trifluoromethyl)-5-methoxy-1H-benzo[D]imidazole

Produkt 1

HCID 589938444-Fluoro-N-[5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyrazin-2-yl]-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Into a 50 mL 3-necked round bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1-(5-bromo-pyrazin-2-yl)-5-methoxy-2-trifluoromethyl-1H-benzoimidazole (iv) (100 mg, 0.27 mmol) in 1,4-dioxane (30 mL). To this was added 4-fluorobenzamide (80 mg, 0.58 mmol), K3PO4 (250 mg, 1.18 mmol), CuI (10 mg, 0.05 mmol) and ethane-1,2-diamine (EDA) (5 mg, 0.08 mmol). The resulting solution was stirred at reflux overnight. The reaction progress was monitored by TLC (EtOAc/PE=1:2). When the reaction had gone to completion, the mixture was filtered to remove the solid components, then concentrated under vacuum. The residue was dissolved in EtOAc, then washed with water. The organic layer was dried over Na2SO4, then concentrated to yield a crude product. The crude product was purified by eluting through a column with a 1:6 EtOAc/PE solvent system. This resulted in 60 mg (52%) of 4-fluoro-N-(5-(5-methoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyrazin-2-yl)benzamide (Compound 86) as a white solid

Aufarbeitung

  1. customInto a 50 mL 3-necked round bottom flask, purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureat reflux overnight
  4. filtrationthe mixture was filtered
  5. customto remove the solid components
  6. concentrationconcentrated under vacuum
  7. dissolutionThe residue was dissolved in EtOAc
  8. washwashed with water
  9. dry with materialThe organic layer was dried over Na2SO4
  10. concentrationconcentrated
  11. customto yield a crude product
  12. customThe crude product was purified
  13. washby eluting through a column with a 1:6 EtOAc/PE solvent system

Quellen und Nachweise

ORD-Eintrag
ord-d41f1ba6bd084c3380752f5d5b2c264d
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614321B2

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