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

HRID 552168

Reaktionsgleichung

Reaktionsgleichung von HRID 552168
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(#N)C>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:28]3[CH2:29][CH2:30][CH:25]([C:23](=[O:24])[C:20]4[CH:19]=[CH:18][C:17]([F:16])=[CH:22][CH:21]=4)[CH2:26][CH2:27]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Produkt 1

HCID 116253966-[4-(4-Fluorobenzoyl)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. customThe residue obtained upon the evaporation of solvent
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e3bb0416ff3a4852a8a6d7e2bd40bb10
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951805B2

Verknüpfte Notizen

Wird geladen…