Potassium Carbonate → 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one
Reaction equation
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[CH:6]=[CH:5][N:4]=1.[SH:12][C:13]1[NH:17][C:16]2[CH:18]=[C:19]3[C:23](=[CH:24][C:15]=2[N:14]=1)[C:22]([CH3:26])([CH3:25])[C:21](=[O:27])[C:20]3([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][S:12][C:13]2[NH:14][C:15]3[CH:24]=[C:23]4[C:19](=[CH:18][C:16]=3[N:17]=2)[C:20]([CH3:28])([CH3:29])[C:21](=[O:27])[C:22]4([CH3:26])[CH3:25])[C:8]=1[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 690 mg of 2-chloromethyl-3-methyl-4--methoxypyridine and 400 mg of 5,7-dihydro-2-mercapto-5,5,7, 7-tetramethylindeno[5,6-d]imidazol-6(lH)-one in 40 ml of absolute acetone was treated with 1.9 g of finely ground potassium carbonate, whereupon the mixture was stirred at room temperature under argon for 18 hours. After concentrating the mixture in vacuo the residue was chromatographed on silica gel with methylene chloride/ethyl acetate (10:1) as the elution agent, the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. By recrystallization from ethyl acetate/ ether there was obtained 5,7-dihydro-2-[[(4-methoxy-3-methyl-2 -pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(lH)-one of melting point 218-220° .
Workup
- concentrationAfter concentrating the mixture in vacuo the residue
- customwas chromatographed on silica gel with methylene chloride/ethyl acetate (10:1) as the elution agent
- customthe pressure being produced with nitrogen gas
- customBy recrystallization from ethyl acetate/ ether there
Sources & evidence
- ORD record
- ord-dc016b47f6fc4eeebf9cb813e3e25ac0
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04981861
Reaction notes
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