Dimethylformamide → 2-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one

HRID 1477217Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[N:15][NH:16][C:17]3=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Cl[CH2:24][C:25]1[O:29][N:28]=[C:27]([CH3:30])[N:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O.O>[CH3:30][C:27]1[N:26]=[C:25]([CH2:24][N:16]2[N:15]=[CH:14][C:13]3[C:18](=[CH:19][C:10]([C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:5][CH:6]=4)=[CH:11][CH:12]=3)[C:17]2=[O:20])[O:29][N:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one (50 mg, 0.163 mmol), 5-(chloromethyl)-3-methyl-1,2,4-oxadiazole (47.5 mg, 0.359 mmol), and potassium carbonate (68 mg, 9.68 mmol) was added DMF (1 mL) and the reaction was heated to 80° C. overnight. The reaction was diluted with EtOAc and water, the layers were separated, and the organic layer was concentrated to an oil. The residue was purified by flash chromatography (Rf=0.32, 1:1 hexanes/ethyl acetate) to afford 2-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one as a white solid. C19H13F3N4O3. 403.1 (M+1). 1H NMR (DMSO) δ 8.58 (s, 1H), 8.48 (d, J=2.0 Hz, 1H), 8.34 (dd, J=2.0, 8.4 Hz, 1H), 8.12 (d, J=8.4 Hz, 1H), 7.98-8.02 (m, 2H), 7.54 (d, J=8.0 Hz, 1H), 5.67 (s, 2H), 2.31 (s, 1H).

Workup

customthe layers were separated
concentrationthe organic layer was concentrated to an oil
customThe residue was purified by flash chromatography (Rf=0.32, 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-5143c11f918040388458920779cabc13
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403782B2

Reaction notes

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