1,2-Dichloroethane → 9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one

HRID 221983

Reaktionsgleichung

[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7](=[O:13])[NH:8]2)[NH2:2].[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[C:26](O)=O.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.CC(O)=O>[C:14]1([C:6]2[C:7](=[O:13])[NH:8][C:9]3[CH:10]=[CH:11][N:12]4[C:26]([C:21]5[N:22]=[CH:23][CH:24]=[CH:25][N:20]=5)=[N:2][N:1]=[C:3]4[C:4]=3[CH:5]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a mixture of 5-hydrazino-3-phenyl-1,6-naphthyridine-2(1H)-one (2-3) (1.4 g, 5.55 mmol), 2-pyrimidinecarboxylic acid (0.69 g, 5.55 mmol), HOBt (0.85 g, 5.55 mmol), and DIPEA (0.97 mL, 5.55 mmol) in DMF (50 mL) was added EDC (1.23 g, 6.66 mmol). After stirring for overnight, AcOH (5 mL) was added, and the mixture was heated under microwave irradiation at 150° C. for 15 minutes. The solvent was removed under reduced pressure, and the residue was diluted with MeOH, and added water. The resulting solid was collected by filtration to give 9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one (2-4) as a colorless solid.

Aufarbeitung

customThe solvent was removed under reduced pressure
additionthe residue was diluted with MeOH
additionadded water
filtrationThe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-b6e29215f372433f9ed8b85f18948545
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08207169B2

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