Isopropyl iodide → (1-isopropyl-1H-benzo[d]imidazol-2-yl) (4-(3-morpholinopyrazin-2-yloxy)phenyl)methanone

HRID 2191927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191927
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+].I[CH:38]([CH3:40])[CH3:39]>CN(C=O)C>[CH:38]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[C:24]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:17]=1)=[O:11])([CH3:40])[CH3:39]

Komponenten

5

Edukt 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium CarbonateHCID 462079381h-Benzimidazol-2-Yl(4-{[3-(Morpholin-4-Yl)pyrazin-2-Yl]oxy}phenyl)methanone

Produkt 1

HCID 46207942(1-isopropyl-1H-benzo[d]imidazol-2-yl) (4-(3-morpholinopyrazin-2-yloxy)phenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of (1H-benzo[d]imidazol-2-yl)(4-(3-morpholinopyrazin-2-yloxy)-phenyl)methanone (115 mg, 286 μmol), potassium carbonate (79.2 mg, 573 μmol) and 2-iodopropane (97.4 mg, 573 μmol) in DMF (2 mL) was stirred overnight. Additional isopropyl iodide was added until the starting material was consumed. The mixture was diluted with water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate and the combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage™, 10-30% acetone/hexanes gradient, to give (1-isopropyl-1H-benzo[d]imidazol-2-yl) (4-(3-morpholinopyrazin-2-yloxy)phenyl)methanone. MS (ESI, pos. ion) m/z: 444.1 (M+1). IC50 (uM) ++++.

Aufarbeitung

  1. customwas consumed
  2. additionThe mixture was diluted with water and ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by Biotage™, 10-30% acetone/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-cfc3a425581b422fbee17b4f25ceae0e
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329700B2

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