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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 79516Erstellt: 25. Oktober 2026

Triethylamine → (R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridine-5-carboxylate

https://huagongshe.com/reaction/79516

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
Edukt1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Edukt1-Hydroxybenzotriazole hydrateHCID 2796029—
EduktN-Boc-4-chloro-D-phenylalanineHCID 7018791—
Eduktmethyl 4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylateHCID 68762011—
LösungsmittelDichloromethaneHCID 6344—
Produkt(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridine-5-carboxylateHCID 6876522129,4%

Reaktionsschritte

Methyl 4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.23 g, 0.69 mmol) and (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.227 g, 0.759 mmol) were placed in DCM (5 mL) at room temperature. HOBT-H2O (0.147 g, 0.966 mmol), EDCI (0.172 g, 0.897 mmol) and triethylamine (0.48 mL, 3.45 mmol) were then added, and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give a crude residue. The residue was purified by column chromatography (500:7 DCM:MeOH) to give (R)-methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.11 g, 29.4% yield).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08841304B2
Quelldatensatzuspto-grants-2014_09
ORD IDord-0f0cfbb3cb3e48468f0960affb63a006
Quellennotizuspto-grants-2014_09