HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Hydrochloric Acid → (4Z,7Z,10Z,13Z,16Z,19Z)-N-(3-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)amino)-3-oxopropyl)docosa-4,7,10,13,16,19-hexaenamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | Doconexent | HCID 445580 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Edukt | 3-amino-N-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-yl]propanamide | HCID 70945222 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | (4Z,7Z,10Z,13Z,16Z,19Z)-N-(3-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)amino)-3-oxopropyl)docosa-4,7,10,13,16,19-hexaenamide | HCID 70945382 | — |
Reaktionsschritte
The HCl salt of 3-amino-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)propanamide (0.1 mmol) is taken up in 5 mL of DMF along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 0.1 mmol), HATU (0.11 mmol) and DIEA (0.3 mmol). The resulting reaction mixture is stirred at room temperature for 4 h and then diluted with EtOAc (20 mL). The organic layer is washed with water (3×5 mL), brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by silica gel chromatography (95% CH2Cl2, 5% MeOH) affords (4Z,7Z,10Z,13Z,16Z,19Z)-N-(3-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)amino)-3-oxopropyl)docosa-4,7,10,13,16,19-hexaenamide.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09029548B2 |
| Quelldatensatz | uspto-grants-2015_05 |
| ORD ID | ord-5f0fc95891ac4e98b4c5c22c2b17f4af |
| Quellennotiz | uspto-grants-2015_05 |