HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-[(2S)-1-Hydroxy-4-methylpentan-2-yl]-1H-isoindole-1,3(2H)-dione → (S)-2-(1-((4,6-dimethyl-5-oxo 5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-[(2S)-1-Hydroxy-4-methylpentan-2-yl]-1H-isoindole-1,3(2H)-dione | HCID 71378922 | — |
| Reactant | 8-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-one | HCID 86710337 | — |
| Product | (S)-2-(1-((4,6-dimethyl-5-oxo 5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione | HCID 86710374 | 49% |
Reaction Steps
8-Chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (1.4 g, 5.41 mmol) and (S)-2-(1-hydroxy-4-methylpentan-2-yl)isoindoline-1,3-dione (4.01 g, 16.23 mmol) were subjected to Buchwald coupling as described in Example 16, Part H) to give (S)-2-(1-((4,6-dimethyl-5-oxo 5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione as yellow solid (1.4 g, 2.62 mmol, 49% yield). LC/MS (ESI) m/e 470.2 [(M+H)+, calcd for C28H28N3O4 470.2]; LC/MS retention time (method C): tR=2.05 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08901305B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-ebb0125c28944f5c84f9be83705d81ca |
| Source note | uspto-grants-2014_12 |