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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 552168Erstellt: 23. Oktober 2026

Triethylamine → 6-[4-(4-Fluorobenzoyl)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

https://huagongshe.com/de/reaction/552168

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
Edukt4-(4-Fluorobenzoyl)piperidineHCID 2724440—
Edukt6-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamideHCID 65561565—
LösungsmittelAcetonitrileHCID 6342—
Produkt6-[4-(4-Fluorobenzoyl)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amideHCID 1162539685%

Reaktionsschritte

A mixture of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.500 g, 2.22 mmol), (4-fluorophenyl)piperidin-4-ylmethanone (0.620 g, 2.55 mmol) and triethylamine (0.7 mL, 5 mmol) in acetonitrile (20 mL) was heated to reflux overnight. The solvent was removed in vacuo. The residue was diluted with water, then extracted with ethyl acetate. The residue obtained upon the evaporation of solvent was purified by column chromatography. The title compound was obtained as a white solid in 85% yield (0.270 g). 1H NMR (300 MHz, CDCl3) δ 8.26 (d, J=9.0 Hz, 1H), 8.02-7.93 (m, 2H), 7.65 (d, J=9.0 Hz, 1H), 7.2-7.11 (m, 2H), 6.98 (d, J=9.0 Hz, 1H), 4.55-4.44 (m, 2H), 3.63-3.49 (m, 3H), 3.32-3.19 (m, 2H), 2.5-1.8 (m, 2H), 1.7-1.44 (m, 4H), 0.8-0.67 (m, 1H), 0.52-0.41 (m, 2H), 0.15-0.07 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 200.1, 167.5, 164.1, 163.2, 161.4, 159.9, 158.9, 151.8, 144.6, 132.0, 131.0, 130.9, 129.4, 128.0, 126.9, 116.1, 115.8, 112.2, 44.5, 43.1, 40.0, 39.6, 34.5, 34.3, 27.9, 8.64, 8.6, 4.2. MS (ES+) m/z 397 (M+1).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07951805B2
Quelldatensatzuspto-grants-2011_05
ORD IDord-e3bb0416ff3a4852a8a6d7e2bd40bb10
Quellennotizuspto-grants-2011_05