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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1783968Erstellt: 25. Oktober 2026

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one → 5-(8-(6-(4-Isopropylpiperazin-1-yl)pyridin-3-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)isoindolin-1-one

https://huagongshe.com/reaction/1783968

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 21955795—
Edukt4-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57589928—
Edukt(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[6-(4-isopropylpiperazin-1-yl)pyridin-3-yl]amineHCID 57590080—
KatalysatorHCID 178418397HCID 178418397—
LösungsmittelSodium CarbonateHCID 10340—
Lösungsmittel1,4-DioxaneHCID 31275—
Produkt5-(8-(6-(4-Isopropylpiperazin-1-yl)pyridin-3-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)isoindolin-1-oneHCID 24890645—

Reaktionsschritte

This compound may be prepared using methods as described for Compound 6, step 4, using 5-bromo-N-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (50 mg, 0.12 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (56 mg, 0.216 mmol) and Pd(PPh3)4 (35 mg, 0.03 mmol) in 1.5M Na2CO3 (0.64 mL) and dioxane (2 mL). The crude product is purified by silica gel column chromatography eluting with 95:5 DCM:MeOH followed by 90:10 DCM:MeOH. The title compound is obtained after trituration with a 10:1 mixture n-hexane:DCM (19 mg, 34%). Conversion into the mesylate salt, using 0.1M methanesulfonic acid (0.35 mL), gives the title compound as a yellow solid (20 mg, 69%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07501411B2
Quelldatensatzuspto-grants-2009_03
ORD IDord-bd472570412c4388a8695015086d4763
Quellennotizuspto-grants-2009_03