Oxalyl chloride → N-methyl-4-[4-[(E)-4,4,5,5-tetrafluoropent-2-enoyl]piperazin-1-yl]pyridine-2-carboxamide
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.Cl.[CH3:19][NH:20][C:21]([C:23]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:26]=[CH:25][N:24]=1)=[O:22].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:19][NH:20][C:21]([C:23]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][N:32]([C:5](=[O:7])/[CH:4]=[CH:3]/[C:2]([F:1])([F:11])[CH:8]([F:10])[F:9])[CH2:31][CH2:30]2)[CH:26]=[CH:25][N:24]=1)=[O:22]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-4,4,5,5-tetrafluoropent-2-enoic acid (19 mg, 0.11 mmol) was dissolved in DCM (1 ml), oxalyl chloride was added (9 μl, 0.11 mmol) followed by a drop of DMF. The mixture was stirred for 10 minutes at room temperature. N-methyl-4-piperazin-1-yl-pyridine-2-carboxamide hydrochloride (25.6 mg, 0.1 mmol) was dissolved in DMF (0.5 ml), the mixtures were combined, diisopropylethylamine (75 μl, 0.4 mmol) was added and the resulting mixture was stirred at room temperature for 1 hour. The mixture was evaporated to dryness under reduced pressure, the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 20.2 mg (0.054 mmol, 54%).
Workup
- stirringthe resulting mixture was stirred at room temperature for 1 hour
- customThe mixture was evaporated to dryness under reduced pressure
- customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
- customto yield 20.2 mg (0.054 mmol, 54%)
Sources & evidence
- ORD record
- ord-13210a72890846eb8d8fe909b79d9e75
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883791B2
Reaction notes
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