Acetic Anhydride → 2,2-Dimethylpropyl 4-[4-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate
Reaction equation
[C:1](OC(=O)C)(=O)[CH3:2].[NH2:8][C:9](=[N:30][OH:31])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]2)[CH:11]=1>>[CH3:1][C:2]1[O:31][N:30]=[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:23])[CH2:18][CH2:17]3)[CH:11]=2)[N:8]=1Participants
3
Procedure
Acetic anhydride (3 mL) was added to 2,2-dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}piperazine-1-carboxylate (215 mg) obtained in Example 26-1), and heated under reflux for 2 hours, then the excess acetic anhydride was evaporated away, the residue was diluted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through silica gel column chromatography (hexane/ethyl acetate=7/3) to obtain 36 mg of the entitled compound as a colorless solid.
Workup
- temperatureheated
- temperatureunder reflux for 2 hours
- customthe excess acetic anhydride was evaporated away
- additionthe residue was diluted with ethyl acetate
- washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
- dry with materialdried with anhydrous sodium sulfate
- customThe solvent was evaporated away
- customthe resulting residue was isolated
- custompurified through silica gel column chromatography (hexane/ethyl acetate=7/3)
Sources & evidence
- ORD record
- ord-e3a9f5b09ed549ada6fcb86beb46eba5
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101618B2
Reaction notes
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