Water → 3-[Bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile

HRID 915041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915041
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[N:13][C:12]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:5]1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1.O>CC(N(C)C)=O>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:19]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:14]2[C:15]([C:17]#[N:18])=[N:16][C:11]([C:6]3[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)=[C:12]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:13]=2)=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 693318746-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-5-phenyl-2-pyrazinecarbonitrile

Produkt 1

HCID 693319503-[Bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

6-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-5-phenyl-2-pyrazinecarbonitrile (14.61 g) was added to a suspension of NaH (60% in oil suspension) (1.36 g) in DMA (36.5 ml) and the mixture was stirred at 20-25° C. for an hour. After addition of 1-(chloromethyl)-4-methoxybenzene (4.82 ml), the mixture was stirred at the same temperature for 20 hours. To the reaction mixture was added water (183 ml) and a precipitate was collected by filtration. The precipitate was purified by column chromatography on silica gel (EtOAc only) to give a solid. The solid was crystallized from a mixture of n-hexane and CHCl3 to give 3-[bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile (16.58 g).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 20 hours
  2. filtrationa precipitate was collected by filtration
  3. customThe precipitate was purified by column chromatography on silica gel (EtOAc only)
  4. customto give a solid
  5. customThe solid was crystallized from a mixture of n-hexane and CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-50d12557b217420f95f60f4dd7f738cf
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265120B2

Notizen zur Reaktion

Wird geladen…