HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sodium Carbonate → 3-Oxo-4-{4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one | HCID 21955795 | — |
| Edukt | 4-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amide | HCID 57589928 | — |
| Edukt | 4-[4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester | HCID 86619664 | — |
| Katalysator | HCID 178418397 | HCID 178418397 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Lösungsmittel | Sodium chloride; water | HCID 57417360 | — |
| Produkt | 3-Oxo-4-{4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester | HCID 67047599 | 47% |
Reaktionsschritte
This compound may be prepared using methods as described for Compound 6, step 4, using 4-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (115 mg, 0.24 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (92 mg, 0.35 mmol), and Pd(PPh3)4 (83 mg, 0.072 mmol) in 1.5M Na2CO3 (aq) (1.3 mL, 1.92 mmol), and dioxane (2.5 mL). The reaction mixture is diluted with brine then toluene is added and a precipitate is formed and collected by filtration. The resultant solid is dissolved in DCM and filtered through a silica cartridge to afford the title compound as a yellow solid (60 mg, 47%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07915256B2 |
| Quelldatensatz | uspto-grants-2011_03 |
| ORD ID | ord-51d75768b34a416a811d709fcd73ba6b |
| Quellennotiz | uspto-grants-2011_03 |