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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1297461Erstellt: 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/1297461

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,2-DichloroethaneHCID 11—
EduktWaterHCID 962—
Edukt1-HydroxybenzotriazoleHCID 75771—
EduktDiisopropylethylamineHCID 81531—
Edukt1-(2-hydroxyethyl)-3-(methylaminomethyl)-1H-indoleHCID 22139005—
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 6678074827,1%

Reaktionsschritte

EDC (0.54 g, 2.80 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 (0.71 g, 2.80 mmole), 1-(2-hydroxyethyl)-3-(methylaminomethyl)-1H-indole (0.52 g, 2.55 mmole), HOBt.H2O (0.38 g., 2.80 mmole) and diisopropylethylamine (1.11 mL, 6.40 mmole) in DMF (25 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 (20% EtOH/EtOAc) gave title compound (0.28 g, 27%) as an off-white solid after drying in vacuo: MS (ES) m/e 405 (M+H)+.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07250424B2
Quelldatensatzuspto-grants-2007_07
ORD IDord-1cf5545776394d77b9c17717ae4cee44
Quellennotizuspto-grants-2007_07