Water → 4-(4-tert-butoxycarbonyl-1-piperazinyl)-methyl-6-(3-fluoro-4-methylphenyl)-2-isobutyl-2H-pyridazin-3-one

HRID 1348695Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11](COS(C)(=O)=O)[C:12](=[O:19])[N:13]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C:26](=O)([O-])[O-].[K+].[K+].[N:32]1([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.O>C(#N)C>[C:41]([O:40][C:38]([N:32]1[CH2:37][CH2:36][N:35]([C:11]2[C:12](=[O:19])[N:13]([CH2:15][CH:16]([CH3:17])[CH3:18])[N:14]=[C:9]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([F:1])[CH:3]=3)[C:10]=2[CH3:26])[CH2:34][CH2:33]1)=[O:39])([CH3:44])([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(3-fluoro-4-methylphenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one (100 mg, 0.27 mmol) in acetonitrile (1 mL) were added potassium carbonate (56.3 mg, 0.41 mmol) and tert-butyl 1-piperazinecarboxylate (60.7 mg, 0.33 mmol), and the mixture was stirred at 80° C. for 2 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and then, water was added. The mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel [chloroform/methanol (40/1)] to yield the title compound as a yellow oil (115 mg, 92.4%).

Workup

customto drop back to room temperature
extractionThe mixture was extracted with chloroform
dry with materialThe extract was dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by column chromatography on silica gel [chloroform/methanol (40/1)]

Sources & evidence

ORD record: ord-2ee57589ebeb4414acbb49466d8c0835
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211577B2

Reaction notes

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