Sodium hydride → HCID 51042485, Verbindung

HRID 1875718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875718
[H-].[Na+].[CH:3]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:11]1[C:16]([C:17]2[N:21]([CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:20]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:19]=3[N:18]=2)=[CH:15][CH:14]=[CH:13][N:12]=1>CN(C)C=O>[CH:23]1([CH2:22][N:21]2[C:20]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:19]=3[N:18]=[C:17]2[C:16]2[C:11]([O:9][CH2:8][CH:3]3[CH2:7][CH2:6][CH2:5][CH2:4]3)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 77195CyclopentanemethanolHCID 866522862-(2-chloro-pyridin-3-yl)-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole

Produkt 1

HCID 51042485HCID 51042485, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a suspension of sodium hydride (20 mg, 0.51 mmol, 60%) in dry N,N-dimethylformamide (5 ml) at 25° C. was slowly added a solution of cyclopentyl-methanol (30 mg, 0.30 mmol; CAS Reg. No. 3637-61-4) in dry N,N-dimethylformamide (5 ml) and the suspension was stirred for 0.5 h. A solution of 2-(2-chloro-pyridin-3-yl)-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole (90 mg, 0.25 mmol) in N,N-dimethylformamide (5 ml) was then added drop wise to the above solution and further stirred for 16 h at 25° C. The reaction mixture was quenched with saturated aqueous solution of ammonium chloride. The solvents were removed under reduced pressure. The crude material dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel (20-30% ethyl acetate/n-hexane) to afford the title compound as a colorless solid (54%). MS (Turbo Spray): m/z=426.3 (M+H).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated aqueous solution of ammonium chloride
  2. customThe solvents were removed under reduced pressure
  3. dissolutionThe crude material dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography over silica gel (20-30% ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-78dd30227a6845f49dcd3c42d5706937
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309581B2

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