HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl Carbamate → N-[7-(4-piperidinyl)oxy-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl Carbamate | HCID 11722 | — |
| Reactant | Piperidin-4-ol | HCID 79341 | — |
| Reactant | Methanesulfonate | HCID 85257 | — |
| Reactant | 7-Iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide | HCID 66892506 | — |
| Reactant | 7-hydroxy-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide | HCID 68857119 | — |
| Catalyst | Copper | HCID 23978 | — |
| Solvent | Methyl 4-[(5-{[(2-methoxy-5-methylphenyl)amino]sulfonyl}-1-benzofuran-7-yl)oxy]piperidine-1-carboxylate | HCID 68855386 | — |
| Product | N-[7-(4-piperidinyl)oxy-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide | HCID 11983287 | — |
Reaction Steps
Hydrolysis of 7-iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide in alkaline solution using copper as catalyst results in 7-hydroxy-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide. Reaction with a methyl carbamate protected mesylate of 4-hydroxypiperidine, results in methyl 4-[(5-{[(2-methoxy-5-methylphenyl)amino]sulfonyl}-1-benzofuran-7-yl)oxy]piperidine-1-carboxylate, which is hydrolysed in alkaline solution giving the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07582767B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-99e6b72eb0594a5892ca4dbe0334a43e |
| Source note | uspto-grants-2009_09 |