HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate | HCID 3086116 | — |
| Reactant | 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one | HCID 22124513 | — |
| Product | 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester | HCID 53996632 | 69.5% |
Reaction Steps
To a solution of 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one (200 mg in 5 mL dicloroethane) was added 136 mg of 2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate followed by 0.092 mL diisopropylethylamine and the mixture heated to reflux. After 20 hours, the reaction was cooled to room temperature, concentrated in vacuo and purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1) to give the title compound (183 mg.)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06150352 |
| Source dataset | uspto-grants-2000_11 |
| ORD ID | ord-0ea4e2d319264667830ec9f4f8c2e71f |
| Source note | uspto-grants-2000_11 |