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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 18335Erstellt: 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/18335

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,2-DichloroethaneHCID 11—
EduktDiisopropylethylamineHCID 81531—
Edukt1-Hydroxybenzotriazole hydrateHCID 2796029—
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
PatentnummerUS07741339B2
Quelldatensatzuspto-grants-2010_06
ORD IDord-77f03fd9110d487487fee87e3dd752ea
Quellennotizuspto-grants-2010_06