HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → {2-[5-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ethyl{2-[5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate | HCID 68090828 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | {2-[5-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid | HCID 58081059 | 95% |
Reaction Steps
A mixture of ethyl{2-[5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (690 mg), 1M aqueous sodium hydroxide solution (5 mL), ethanol (5 mL) and tetrahydrofuran (5 mL) was stirred at room temperature for 15 hr. To the reaction solution was added 1M hydrochloric acid (5 mL) and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crystals were washed with hexane-ethyl acetate mixed solvent to give the title compound (610 mg, yield 95%) as brown crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08557805B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-006779211244446780ad5956d927dcfd |
| Source note | uspto-grants-2013_10 |