(E)-4-methylhex-2-enoic Acid → (E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

HRID 333985Notes

Reaction equation

HRID 333985 reaction equation
[CH3:1][CH:2]([CH2:8][CH3:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[N:10]1([C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>CN(C=O)C.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>[CH3:1][CH:2]([CH2:8][CH3:9])/[CH:3]=[CH:4]/[C:5]([N:13]1[CH2:14][CH2:15][N:10]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([F:29])([F:27])[F:28])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH2:11][CH2:12]1)=[O:7]

Participants

6

Reactant 2

HCID 5463168(E)-4-methylhex-2-enoic AcidHCID 114602054-Piperazin-1-yl-7-(trifluoromethyl)quinoline

Product 1

HCID 86691602(E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)Solvent

Procedure

(E)-4-Methylhex-2-enoic acid (26 mg, 0.2 mmol) was dissolved in DMF (0.5 ml) together with diisopropylethylamine (35 μl), HATU was added (76 mg, 0.2 mmol) and the mixture was stirred at room temperature for 15 minutes. 4-piperazin-1-yl-7-(trifluoromethyl)quinoline (56 mg, 0.2 mmol) was dissolved in DMF (0.5 ml) together with diisopropylethylamine (35 μl), the two solutions were combined and stirred at room temperature overnight. The mixture was evaporated to dryness under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 62.6 mg (0.16 mmol, 80%). MS (APCI) m/z=391.9 [M+1]+.

Workup

  1. additionwas added (76 mg, 0.2 mmol)
  2. stirringstirred at room temperature overnight
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  5. customto yield 62.6 mg (0.16 mmol, 80%)

Sources & evidence

ORD record
ord-ffcff14e00e84e19a9757aa08db5402d
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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