HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 7-chloro-3-(3,5-dimethylphenyl)-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester | HCID 53659552 | — |
| Catalyst | Anisole | HCID 7519 | — |
| Product | 7-chloro-3-(3,5-dimethylphenyl)-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one | HCID 22124505 | 92.3% |
Reaction Steps
To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (9.0 mg in 2.0 dry methylene chloride) was added a few drops of anisole followed by 1.0 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 30 minutes the solvents were removed in vacuo and the resulting residue purified by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 9:1) to give the title compound (7.0 mg). MASS: 536 (M+H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06150352 |
| Source dataset | uspto-grants-2000_11 |
| ORD ID | ord-6e53d0022f4640e78222148e7323de31 |
| Source note | uspto-grants-2000_11 |