HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-Chloro-N-{2-methyl-3-[3-(methyloxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-4-yl}benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3-Chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide | HCID 68323763 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-Chloro-N-{2-methyl-3-[3-(methyloxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-4-yl}benzenesulfonamide | HCID 68323824 | 59.1% |
Reaction Steps
Alternatively, a solution of 3-chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 115) (710 mg, 1.495 mmol) in 37% HCl (8 mL, 97 mmol) was heated to 100° C. under nitrogen atmosphere overnight. The reaction mixture was cooled to RT, diluted with DCM (ca. 50 mL) and washed with water (ca. 50 mL×2). The combined aqueous layer was re-extracted with DCM (ca. 25 mL) and the combined organic layers passed through phase separator and the solvent concentrated in vacuo. The residue was further triturated with DCM, to afford the title compound (407 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029545B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-d8673b562dac4012a33348128e2f778a |
| Source note | uspto-grants-2015_05 |