Omeprazole → 1-[(benzotriazol-1-yl)methyl]-6-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

Participants

Reaction Conditions

Reaction Steps

5-Methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (172 mg) was dissolved in 20 ml of dichloromethane. Sodium tert-butoxide (55 mg) and 1-(chloromethyl)-1H-benzotriazole (85 mg) was added. The reaction mixture was stirred at 30° C. for 3 days. TLC analysis (developing solvent; chloroform-methanol 15:1) showed major one spot of 1-[(benzotriazol-1-yl)methyl]-5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole above 5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole. The titled product was purified by preparative thin layer chromatography. 195 mg of product, a mixture of 1-[(benzotriazol-1-yl)methyl]-5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole and 1-[(benzotriazol-1-yl)methyl]-6-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole was obtained (3:2 ratio).

Provenance & Evidence