Triphenylphosphine → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-3,5-difluoro-benzonitrile

HRID 417137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417137
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:14][O:15]CC3CCCCC3)[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[F:35][C:36]1[CH:37]=[C:38]([CH:41]=[C:42]([F:44])[CH:43]=1)[C:39]#[N:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:14][O:15][C:43]3[C:36]([F:35])=[CH:37][C:38]([C:39]#[N:40])=[CH:41][C:42]=3[F:44])[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 5872043,5-DifluorobenzonitrileHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Produkt 1

HCID 666192254-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-3,5-difluoro-benzonitrile

Versuchsvorschrift

The title compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Example 1, intermediate c), 3,5-difluorobenzonitrile (commercially available), triphenylphosphine and di-tert-butyl azodicarboxylate. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:tert-butyl methyl ether (100:0 to 50:50). The product-containing fractions were pooled and chromatographed on a preparative HPLC system (Phenomenex Gemini column) using a gradient of acetonitrile and water. Colorless foam (49%). MS (Turbo Spray): m/z=528.1 [M+H].

Aufarbeitung

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:tert-butyl methyl ether (100:0 to 50:50)
  3. customchromatographed on a preparative HPLC system (Phenomenex Gemini column)

Quellen und Nachweise

ORD-Eintrag
ord-699a5059576048b59e5be731bee34137
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088930B2

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