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

HRID 411620

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[NH:7][C:8]([S:10]([CH2:12][C:13]3[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=3)=[O:11])=[N:9][C:5]=2[CH:4]=1.CC(C)([O-])C.[Na+].Cl[CH2:32][N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[N:34]1.N1(CN2C3C=CC(OC)=CC=3N=C2S(CC2C(C)=C(OC)C(C)=CN=2)=O)C2C=CC=CC=2N=N1>ClCCl.C(Cl)(Cl)Cl.CO>[N:33]1([CH2:32][N:9]2[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:24]=[CH:23][C:6]=3[N:7]=[C:8]2[S:10]([CH2:12][C:13]2[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=2)=[O:11])[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[N:34]1

Participants

Conditions

Temperature: 30 °C

Procedure

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).

Workup

customThe titled product was purified by preparative thin layer chromatography
addition195 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

Sources & evidence

ORD record: ord-1b68d613025a437985ac12dc9d4fd244
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559167B1

Linked notes

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