Diisopropylethylamine → (NZ)-4-acetyl-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]piperazine-1-carboxamide
Reaction equation
[I-].[CH3:2][N+:3]1[CH:7]=[CH:6][N:5]([C:8](/[N:10]=[C:11]2\[S:12][C:13]([CH3:26])=[CH:14][N:15]\2[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[O:9])[CH:4]=1.C(N(C(C)C)CC)(C)C.N1([C:42](=[O:44])[CH3:43])CCNCC1>C(#N)C>[C:42]([N:3]1[CH2:7][CH2:6][N:5]([C:8](/[N:10]=[C:11]2\[S:12][C:13]([CH3:26])=[CH:14][N:15]\2[C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:20][CH:21]=2)=[O:9])[CH2:4][CH2:2]1)(=[O:44])[CH3:43]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 20 mL vial were combined a solution of 3-methyl-1-({[(2Z)-5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2(3H)-ylidene]amino}carbonyl)-1H-imidazol-3-ium iodide (45 mg, 0.09 mmol, Example 18B) dissolved in acetonitrile (0.6 mL) and diisopropylethylamine (21 μL, 0.12 mmol) dissolved in acetonitrile (0.6 mL). Then, to the solution was added 1-(piperazin-1-yl)ethanone (13 mg, 0.1 mmol) dissolved in acetonitrile (0.5 mL). The vial was capped and shaken overnight at room temperature. The reaction was checked by LC/MS and concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid) to supply the title compound.
Workup
- customThe vial was capped
- concentrationconcentrated to dryness
- dissolutionThe residue was dissolved in 1:1 DMSO/MeOH
- custompurified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid) to supply the title compound
Sources & evidence
- ORD record
- ord-f30928c7fcdd40eb97347ccee9a5e4d5
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383657B2
Reaction notes
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