Water → 1-(Difluoromethyl)-8-phenyl-[1,2,4]triazolo[4,3-a][1,5]naphthyridin-7(6H)-one

HRID 42377

Reaction equation

[NH:1]([C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:6]2)[NH2:2].[F:20][CH:21]([F:27])[C:22](OCC)=O.FC(F)C(O)=O.O>CN1C(=O)N(C)CC1>[F:20][CH:21]([F:27])[C:22]1[N:4]2[C:5]3[CH:6]=[C:7]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]2=[N:1][N:2]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 6-hydrazino-3-phenyl-1,5-naphthyridin-2(1H)-one (7-2) (21 g, 83 mmol), ethyl difluoroacetate (31 g, 250 mmol), and difluoroacetic acid (200 mg, 2.08 mmol) in DMI (100 mL) was heated under microwave irradiation at 200° C. for 1 h. To the cooled mixture was added water, and the resulting solid was collected by filtration to give 1-(difluoromethyl)-8-phenyl[1,2,4]triazolo[4,3-a]-1,5-naphthyridin-7(6H)-one (10-1) as pale yellow solid.

Workup

filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-bb3372ca47a9425ba89b4ac18a1052b0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536193B2

Linked notes

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