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

HRID 221983

Reaction equation

[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

Participants

Conditions

Temperature: 150 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-b6e29215f372433f9ed8b85f18948545
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207169B2

Linked notes

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