HuagongsheHuagongshe Chemistry Print Report · For research reference only
Omeprazole → 1-[2-acetamido-4-methyl-5-thiazolylsulfonyl]-5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Omeprazole | HCID 4594 | — |
| Reactant | 2-Acetamido-4-methylthiazole-5-sulfonyl chloride | HCID 96951 | — |
| Reactant | MeOH ACN DCM | HCID 22226298 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-[2-acetamido-4-methyl-5-thiazolylsulfonyl]-5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole | HCID 10218459 | 51.7% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06559167B1 |
| Source dataset | uspto-grants-2003_05 |
| ORD ID | ord-7cd2aead064d4e10824ddaf355b363ef |
| Source note | uspto-grants-2003_05 |