1-Propanol → 4-Chloro-5-[3-{3-(4-formylpiperazin-1-yl)-propoxy}-4-methoxybenzylamino]-3(2H)-pyridazinone

HRID 583112

Reaktionsgleichung

Reaktionsgleichung von HRID 583112
[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:16][NH2:17])[CH2:5][CH2:4]1)=[O:2].[Cl:23][C:24]1[C:25](=[O:31])[NH:26][N:27]=[CH:28][C:29]=1Cl.C(N(CC)CC)C.C(O)CC>O>[Cl:23][C:24]1[C:25](=[O:31])[NH:26][N:27]=[CH:28][C:29]=1[NH:17][CH2:16][C:15]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:13]([O:12][CH2:11][CH2:10][CH2:9][N:6]2[CH2:5][CH2:4][N:3]([CH:1]=[O:2])[CH2:8][CH2:7]2)[CH:14]=1

Komponenten

6

Edukt 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 732474,5-Dichloro-3-hydroxypyridazineHCID 196894243-(3-(4-Formylpiperazin-1-yl)-propoxy]-4-methoxybenzylamine

Produkt 1

HCID 158591884-Chloro-5-[3-{3-(4-formylpiperazin-1-yl)-propoxy}-4-methoxybenzylamino]-3(2H)-pyridazinoneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture comprising 11.58 g of 3-[3-(4-formylpiperazin-1-yl)-propoxy]-4-methoxybenzylamine, 5.0 g of 4,5-dichloro-3(2H)-pyridazinone, 4.6 g of triethylamine, 50 ml of n-propanol and 50 ml of water, was refluxed under heating with stirring for 14 hours. The solvent was distilled off under reduced pressure, and an aqueous potassium carbonate solution was added to the obtained residue, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 6.21 g of the above-identified compound as slightly yellow white solid.

Aufarbeitung

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionan aqueous potassium carbonate solution was added to the obtained residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8659d09b1e8e48e6a06d73e5bce93b23
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929074

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