Lawesson's reagent → (E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-ene-1-thione

HRID 333986Notes

Reaction equation

HRID 333986 reaction equation
[CH3:1][CH:2]([CH2:27][CH3:28])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>C1COCC1>[CH3:1][CH:2]([CH2:27][CH3:28])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[S:38]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86691602(E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

Product 1

HCID 86691603(E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-ene-1-thione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-4-methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one (20 mg, 0.049 mmol) was dissolved in THF (1 ml), Lawesson's reagent (20 mg, 0.051 mmol) was added in one portion and the resulting mixture was stirred overnight at room temperature. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 5.4 mg (0.013 mmol, 25%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  3. customto yield 5.4 mg (0.013 mmol, 25%)

Sources & evidence

ORD record
ord-a87e0d5970434aa18618f7618bdc92fd
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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