Oxalyl chloride → (E)-4,4,5,5,5-pentafluoro-N-[2-[(4-methyl-2-pyridyl)amino]ethyl]pent-2-enamide
Reaction equation
[F:1][C:2]([F:12])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH3:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28][NH2:29])[CH:21]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[F:12][C:2]([F:1])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:29][CH2:28][CH2:27][NH:26][C:22]1[CH:21]=[C:20]([CH3:19])[CH:25]=[CH:24][N:23]=1)=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-4,4,5,5,5-Pentafluoropent-2-enoic acid (29 mg, 0.15 mmol) was dissolved in DMF (1 ml), oxalyl chloride was added (13 μl, 0.15 mmol) and the solution was stirred at room temperature for 5 minutes. To this solution was added a solution of N′-(4-methyl-2-pyridyl)ethane-1,2-diamine (19 mg, 0.1 mmol) in DMF (0.5 ml) and diisopropylethylamine (51 μl, 0.3 mmol) and the resulting mixture was stirred at room temperature for two hours. The reaction mixture was diluted with ethyl acetate, washed with sat. sodium bicarbonate solution and brine and dried over magnesium sulfate. The volatiles were removed under reduced pressure and the residue obtained was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile) to yield 18.5 mg (0.057 mmol, 57%).
Workup
- stirringthe resulting mixture was stirred at room temperature for two hours
- washwashed with sat. sodium bicarbonate solution and brine
- dry with materialdried over magnesium sulfate
- customThe volatiles were removed under reduced pressure
- customthe residue obtained
- customwas purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile)
- customto yield 18.5 mg (0.057 mmol, 57%)
Sources & evidence
- ORD record
- ord-8c35979386a74383b5ff2310ce289007
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321724B2
Reaction notes
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