SK&F 105809 → 5h-Pyrrolo[1,2-a]imidazole,6,7-dihydro-2-[4-(methylsulfonyl)phenyl]-3-(4-pyridinyl)-

HRID 1885580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885580
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)=[O:3].[Mn]([O-])(=O)(=O)=[O:25].[K+]>O>[CH3:1][S:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)(=[O:25])=[O:3]

Komponenten

4

Edukt 2

HCID 129725SK&F 105809HCID 516875Potassium Permanganate

Produkt 1

HCID 198792325h-Pyrrolo[1,2-a]imidazole,6,7-dihydro-2-[4-(methylsulfonyl)phenyl]-3-(4-pyridinyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred solution of 0.64 g (1.98 mmoles) of 2-(4-methylsulfinylphenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]pyrrolo[1,2-a]imidazole of Example 4 in water was treated dropwise over 45 minutes with an aqueous solution of 0.209 g (1.32 mmoles) of potassium permanganate. After stirring overnight, the suspension was extracted with methylene chloride. The organic phase was dried over anhydrous potassium carbonate and stripped in vacuo. The residue flash chromatographed in silica eluting with 2 to 4% methanol in chloroform. The solvent was removed in vacuo and the residue recrystallized from ethyl acetate to afford the desired titled compound, mp 222.5°-224° C. 1H NMR (250 MHz, CDCl3) δ 8.62 (2H,d), 7.85 (2H,d), 7.72 (2H,d), 7.26 (2H,d), 4.05 (2H,t), 3.05(s) superimposed upon 3.03(t) (5H total), 2.70 (2H,q).

Aufarbeitung

  1. extractionthe suspension was extracted with methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous potassium carbonate
  3. customThe residue flash chromatographed in silica eluting with 2 to 4% methanol in chloroform
  4. customThe solvent was removed in vacuo
  5. customthe residue recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-26bd276e5cf6432a9997313a77ec3fcc
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05145858

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