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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 79528Erstellt: 25. Oktober 2026

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(5-(3-fluorophenyl)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate

https://huagongshe.com/reaction/79528

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
EduktDiisopropylethylamineHCID 81531—
Edukt1-Hydroxybenzotriazole hydrateHCID 2796029—
EduktN-Boc-4-chloro-D-phenylalanineHCID 7018791—
Edukt5-(3-fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridineHCID 68760402—
LösungsmittelDichloromethaneHCID 6344—
Produkt(R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(5-(3-fluorophenyl)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamateHCID 6876147846,3%

Reaktionsschritte

5-(3-Fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine (0.062 g, 0.168 mmol) and (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.0604 g, 0.201 mmol) were placed in DCM (3 mL) at room temperature. HOBT-H2O (0.0360 g, 0.235 mmol), EDCI (0.0418 g, 0.218 mmol), and DIEA (d 0.742; 0.146 mL, 0.840 mmol) were then added. The reaction was stirred at room temperature for 2 hours. The reaction was then quenched with saturated Na2CO3 and extracted with DCM. The organic fractions were dried, filtered, and concentrated to give a crude oil. The oil was purified by column chromatography (500:5 D CM: MeOH) to give (R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.045 g, 46.3% yield).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08841304B2
Quelldatensatzuspto-grants-2014_09
ORD IDord-29230f5c26974c68aee1097b26a6e3b8
Quellennotizuspto-grants-2014_09