HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 1-[3-(3-Bromophenyl)-7-chloro-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropyl urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 2-{2-[3-(3-Bromophenyl)-7-chloro-6-(3-cyclopropyl-ureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester | HCID 53904408 | — |
| Catalyst | Anisole | HCID 7519 | — |
| Product | 1-[3-(3-Bromophenyl)-7-chloro-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropyl urea | HCID 22129993 | 50.5% |
Reaction Steps
To a solution of 2-{2-[3-(3-bromophenyl)-7-chloro-6-(3-cyclopropyl-ureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (14 mg in 2.0 mL methylene chloride) was added 2 drops of anisole followed by 2.0 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:methanol:ammonium hydroxide, 95:5:1; then 90:10:1) to give the title compound (6.0 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06147088 |
| Source dataset | uspto-grants-2000_11 |
| ORD ID | ord-ae46d8437b244060a09b22e0b0c47e02 |
| Source note | uspto-grants-2000_11 |