HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-(3-{[7-(Benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-{3-[(7-Bromoheptyl)oxy]propyl}benzenesulfonamide | HCID 11509395 | — |
| Reactant | 5-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-one | HCID 69119720 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3-(3-{[7-(Benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamide | HCID 69316214 | 46.1% |
Reaction Steps
5-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-one (48 mg) was dissolved in acetonitrile (2 ml). N,N-diisopropylethylamine (0.042 ml), and 3-{3-[(7-bromoheptyl)oxy]propyl}benzenesulfonamide (43 mg) were added to the solution, which was heated at reflux for 72 h under nitrogen. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were combined, dried (MgSO4) and evaporated in vacuo. The residue was purified on a silica SPE cartridge eluting with ethyl acetate-cyclohexane mixtures to give the title compound (36 mg). LCMS RT=2.76 min
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07402598B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-2607abdb2a9e4138b98ce0e74683c724 |
| Source note | uspto-grants-2008_07 |