Oxalyl chloride → (E)-4,4,5,5-tetrafluoro-N-[2-[[2-methyl-6-(2-methylbutoxy)-4-pyridyl]amino]ethyl]-pent-2-enamide
Reaction equation
[F:1][C:2]([F:11])([CH:8]([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH3:18][C:19]1[CH:24]=[C:23]([NH:25][CH2:26][CH2:27][NH2:28])[CH:22]=[C:21]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])[N:20]=1>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[F:11][C:2]([F:1])([CH:8]([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:28][CH2:27][CH2:26][NH:25][C:23]1[CH:22]=[C:21]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])[N:20]=[C:19]([CH3:18])[CH:24]=1)=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
(E)-4,4,5,5-tetrafluoropent-2-enoic acid (21 mg, 0.12 mmol) was dissolved in DCM (1 ml), oxalyl chloride was added (10 μl, 0.12 mmol) followed by a drop of DMF. The mixture was stirred for 10 minutes at room temperature. N-[2-methyl-6-(2-methylbutoxy)-4-pyridyl]-ethane-1,2-diamine (18 mg, 0.1 mmol) was dissolved in DMF (0.5 ml), the mixtures were combined, TEA (42 μl, 0.3 mmol) was added and the resulting mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate, washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 13 mg of a white solid (0.039 mmol, 39%).
Workup
- stirringthe resulting mixture was stirred at room temperature for 1 hour
- washwashed with water and saturated sodium bicarbonate solution
- dry with materialdried over magnesium sulfate
- customthe solvent was removed under reduced pressure
- customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
Sources & evidence
- ORD record
- ord-8260f32ef9a2436cb6fe49cb3ede1aa6
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
Loading…