SK&F 105809 → 5h-Pyrrolo[1,2-a]imidazole,6,7-dihydro-2-[4-(methylsulfonyl)phenyl]-3-(4-pyridinyl)-
Reaction equation
[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- extractionthe suspension was extracted with methylene chloride
- dry with materialThe organic phase was dried over anhydrous potassium carbonate
- customThe residue flash chromatographed in silica eluting with 2 to 4% methanol in chloroform
- customThe solvent was removed in vacuo
- customthe residue recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-26bd276e5cf6432a9997313a77ec3fcc
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05145858
Reaction notes
Loading…