Oxalyl chloride → (E)-4,4-Difluoro-1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazin-1-yl]pent-2-en-1-one
Reaction equation
[F:1][C:2]([F:11])([CH:8](F)F)/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:19][C:20]1[O:24][N:23]=[C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[N:21]=1>ClCCl.CN(C=O)C>[F:11][C:2]([F:1])([CH3:8])/[CH:3]=[CH:4]/[C:5]([N:28]1[CH2:29][CH2:30][N:25]([C:22]2[N:21]=[C:20]([CH3:19])[O:24][N:23]=2)[CH2:26][CH2:27]1)=[O:7]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-4,4,5,5-Tetrafluoropent-2-enoic acid (31 mg, 0.23 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (20 μl, 0.23 mol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 15 minutes. This solution was added to a solution of 5-methyl-3-piperazin-1-yl-1,2,4-oxadiazole hydrochloride (25 mg, 0.122 mmol) in dichloromethane (2 ml) and the resulting mixture was stirred at room temperature for three hours. The solvent was removed under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 24.3 mg of a solid (0.083 mmol, 69%).
Workup
- stirringthe resulting mixture was stirred at room temperature for three hours
- customThe solvent was removed under reduced pressure
- customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)
Sources & evidence
- ORD record
- ord-fd0d4789dd9b4abb8269d7f1bd9a9429
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260441B2
Reaction notes
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