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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1297463Erstellt: 24. Oktober 2026

1,2-Dichloroethane → (E)-N-[1-(2-hydroxyethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

https://huagongshe.com/de/reaction/1297463

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,2-DichloroethaneHCID 11—
EduktWaterHCID 962—
Edukt1-HydroxybenzotriazoleHCID 75771—
EduktDiisopropylethylamineHCID 81531—
Edukt1-ethyl-3-(methylaminomethyl)-1H-indoleHCID 22139101—
Edukt(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 66905305—
LösungsmittelDimethylformamideHCID 6228—
Produkt(E)-N-[1-(2-hydroxyethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamideHCID 6678074861%

Reaktionsschritte

EDC (0.35 g, 1.81 mmole) was added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride salt (0.42 g, 1.65 mmole), 1-ethyl-3-(methylaminomethyl)-1H-indole (0.31 g, 1.65 mmole), HOBt.H2O (0.24 g., 1.81 mmole) and diisopropylethylamine (0.86 mL, 4.95 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (10% EtOH/EtOAc) gave title compound (0.39 g, 61%) as a light yellow solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07250424B2
Quelldatensatzuspto-grants-2007_07
ORD IDord-679fbe2697d04cedbd378a8e4a45d52b
Quellennotizuspto-grants-2007_07