N-bromobutanimide → 9-Bromo-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

HRID 1629016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629016
[Br:1]N1C(=O)CCC1=O.[F:9][CH:10]([F:40])[O:11][CH:12]([C:17]1[C:22]2[N:23]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]4[C:31]([CH3:39])=[N:32][C:33]([O:37][CH3:38])=[N:34][C:35]=4[CH3:36])[C:24]3=[N:25][C:21]=2[CH:20]=[CH:19][CH:18]=1)[C:13]([F:16])([F:15])[F:14]>C(#N)C.C(=O)([O-])O.[Na+]>[Br:1][C:20]1[C:21]2[N:25]=[C:24]3[N:26]([C:30]4[C:35]([CH3:36])=[N:34][C:33]([O:37][CH3:38])=[N:32][C:31]=4[CH3:39])[CH2:27][CH2:28][CH2:29][N:23]3[C:22]=2[C:17]([CH:12]([O:11][CH:10]([F:9])[F:40])[C:13]([F:16])([F:15])[F:14])=[CH:18][CH:19]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 577860406-[1-(Difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

Produkt 1

HCID 577860939-Bromo-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoleAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (190 mg, 1.07 mmol) was added to a stirred solution of 6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (469 mg, 1.02 mmol) in acetonitrile (5.0 mL) at room temperature, and the mixture was stirred at room temperature for 5 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give a solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as colorless crystals (330 mg, 0.615 mmol, 60%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give a solid, which
  9. customwas recrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-2cd5942eb35d4863b7aaa8652c78dd9c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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