HuagongsheHuagongshe Chemistry Print Report · For research reference only
[(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate → 2-Chloro-N-{2-oxo-1-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methyl]-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | [(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate | HCID 21906825 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-Chloro-N-{2-oxo-1-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methyl]-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide | HCID 135457544 | 87% |
Reaction Steps
N-[1-((2Z)-2-Amino-2-{[(ethoxycarbonyl)oxy]imino}ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 14) was dissolved in 1,4-Dioxane and the solvent distilled off with the oil bath temperature 140° C. This was repeated 4 times. The residual solid was triturated with refluxing Et2O (10 mL) and after cooling filtered, washed with Et2O (10 mL) and hexane (10 mL) to give the title product (184 mg, 87% (2 steps)) as a pale brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07129249B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-0b82fd1174eb448bbf46a6843e94457a |
| Source note | uspto-grants-2006_10 |