Phosphorus oxychloride → 3-Chloro-2-phenyl-9-(3-pyridinyl)[1,2,4]triazolo[4',3':1,6]pyrido-[2,3-b]pyrazine

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Reaktionsgleichung

O[C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][C:15]([NH:18][NH:19][C:20](=O)[C:21]3[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=3)=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O=P(Cl)(Cl)[Cl:30]>C(#N)C>[Cl:30][C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][C:15]3=[N:18][N:19]=[C:20]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[N:14]3[C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of N′-(2-hydroxy-3-phenylpyrido[2,3-b]pyrazin-6-yl)nicotinohydrazide (3-4) (5.8 g, 16.2 mmol) in acetonitrile (1.3 mL) was added POCl3 (7.5 mL, 81 mmol), and stirred at 100° C. for overnight. The solvent was removed under reduced pressure, and to the residue was added CHCl3 and water. The organic layer was separated, dried (Na2SO4), filtered, and evaporated in vacuo. To the residue was added CHCl3, and the resulting solid was collected by filtration to yield 3-chloro-2-phenyl-9-(3-pyridinyl)[1,2,4]triazolo[4′,3′:1,6]pyrido[2,3-b]pyrazine (3-5) as an orange solid.

Aufarbeitung

customThe solvent was removed under reduced pressure
additionto the residue was added CHCl3 and water
customThe organic layer was separated
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
additionTo the residue was added CHCl3
filtrationthe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-a33d3a20a0fc4d15b3082d8170de1785
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08207169B2

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