HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 4-[2-(tert-Butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Phosgene | HCID 6371 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Aminomethyl-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide | HCID 57470787 | — |
| Reactant | 1-[2-(tert-Butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one | HCID 67000052 | — |
| Product | 4-[2-(tert-Butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide | HCID 67000168 | — |
Reaction Steps
A solution of 1-[2-(tert-butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example 21E (110 mg, 0.34 mmol) and diisopropylethylamine (77 μl, 0.44 mmol) in THF (8.0 ml) and a solution of phosgene in toluene (20%, 233 μl, 0.44 mmol) were stirred together for 2 h. A solution of 4-aminomethyl-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide from Example 21D (108 mg, 0.34 mmol) and diisopropylethylamine (77 μl, 0.44 mmol) in THF (5.0 ml) was added and the mixture was stirred for 18 h and evaporated in vacuo. The residue was directly in the next step of the synthesis as described in Example 21G.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08063038B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-2e2e1e3287644e469e75573cdd0329bc |
| Source note | uspto-grants-2011_11 |