Oxalyl chloride → (E)-4,4,4-Trifluoro-N-[3-(4-methyl-2-pyridyl)propyl]but-2-enamide
Reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.Cl.[CH3:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][CH2:25][CH2:26][NH2:27])[CH:19]=1.CCOP(O)N(C(C)C)C(C)C>ClCCl>[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5]([NH:27][CH2:26][CH2:25][CH2:24][C:20]1[CH:19]=[C:18]([CH3:17])[CH:23]=[CH:22][N:21]=1)=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-4,4,4-Trifluorobut-2-enoic acid (64 mg, 0.46 mmol) was dissolved in dichloromethane (1 ml containing one drop of dimethyl formamide), oxalyl chloride was added (40 μl, 0.46 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of 3-(4-methyl-2-pyridyl)propan-1-amine hydrochloride (56 mg, 0.3 mmol) and EDIPA (240 μl, 1.4 mmol) in anhydrous dichloromethane (5 ml) and the resulting mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile) to yield 47 mg of a solid (0.17 mmol, 58% yield)
Workup
- stirringthe resulting mixture was stirred at room temperature for one hour
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile)
Sources & evidence
- ORD record
- ord-81c4550373bd4664b51c70e4b5c9210f
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321724B2
Reaction notes
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