Ethanol → 5-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 869140Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:22])([CH3:21])[CH2:9][NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]([O:19][CH3:20])=O)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[OH2:23].[NH2:24][NH2:25].C(O)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:22])([CH3:21])[CH2:9][NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]3[O:19][C:20](=[O:23])[NH:25][N:24]=3)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a 25 mL round bottom flask was added methyl 6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazine-3-carboxylate (100 mg, 0.3 mmol, 1.0 equiv), hydrazine hydrate (1 mL), and ethanol (5 mL)). The reaction was refluxed for 2 h and concentrated. N,N′-Carbonyldiimidazole (100 mg, 0.6 mmol, 2.0 equiv) and DMF (1 mL) were then added to the crude product and the reaction was heated to 90° C. for 1.5 h. The reaction mixture was directly purified by reverse phase column chromatography to afford 72 mg (67%) of 5-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)-1,3,4-oxadiazol-2(3H)-one as a white solid, m/z=330.0 [M+H].

Workup

temperatureThe reaction was refluxed for 2 h
concentrationconcentrated
customThe reaction mixture was directly purified by reverse phase column chromatography

Sources & evidence

ORD record: ord-9ad058cdc9854e0fb8ec995e949b4006
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

Loading…