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

HRID 411616Notes

Reaction equation

HRID 411616 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.[C:25]([NH:28][C:29]1[S:30][C:31]([S:35](Cl)(=[O:37])=[O:36])=[C:32]([CH3:34])[N:33]=1)(=[O:27])[CH3:26].ClCCl.C(#N)C.CO>ClCCl.C(N(CC)CC)C>[C:25]([NH:28][C:29]1[S:30][C:31]([S:35]([N:7]2[C:6]3[CH:23]=[CH:24][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:9]=[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])(=[O:36])=[O:37])=[C:32]([CH3:34])[N:33]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 4594Omeprazole2×HCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chlorideHCID 22226298MeOH ACN DCM

Product 1

HCID 102184591-[2-acetamido-4-methyl-5-thiazolylsulfonyl]-5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazoleYield 51.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

172 mg of 5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole was dissolved in 10 ml of dichloromethane and 0.4 ml of triethylamine, and 128 mg of 2-acetamido-4-methyl-5-thiazolyl sulfonyl chloride was added. The reaction mixture was stirred at room temperature for 15 hr. Product spot was shown at slightly higher position than 5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole in thin layer chromatography (developing solvent: dichloromethane-acetonitrile-methanol=100: 10: 5). Product was separated by silica gel column chromatography. 145 mg of the titled product was isolated.

Workup

  1. customProduct was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-7cd2aead064d4e10824ddaf355b363ef
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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