Methanol → 2,2-Dimethylpropyl 4-[4-(5-methoxy-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate
Reaction equation
ClC(Cl)(Cl)[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]3)[CH:9]=2)[N:4]=1.[H-].[Na+].[Cl-].[NH4+].[CH3:34][OH:35]>>[CH3:34][O:35][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:21])[CH2:18][CH2:19]3)[CH:9]=2)[N:4]=1Participants
5
Reactant 4
Product 1
Procedure
2,2-Dimethylpropyl 4-[4-(5-trichloromethyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate (106 mg) obtained in Example 32 was dissolved in methanol (2 mL), and oily sodium hydride (10 mg) was added thereto and stirred at room temperature for 15 minutes, and then aqueous saturated ammonium chloride solution was added to it and extracted with ethyl acetate. The organic layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 2.5 mg of the entitled compound as a colorless oil.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated saline water
- dry with materialdried with anhydrous sodium sulfate
- customThe solvent was evaporated away
- customthe resulting residue was isolated
- custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)
Sources & evidence
- ORD record
- ord-0044f945fa32425784d6b6404fd567fb
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101618B2
Reaction notes
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