Lawesson's reagent → (E)-4,4,4-Trifluoro-1-[4-(4-methyl-2-pyridyl)piperazin-1-yl]but-2-ene-1-thione

HRID 1775364Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1COCC1>[F:1][C:2]([F:21])([F:20])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[S:31]

Participants

Conditions

Temperature: 110 °C

Procedure

The residue of step A was dissolved in anhydrous THF (2 ml), Lawesson's reagent (40 mg, 0.2 mmol) was added and the mixture was stirred at 110° C. in closed vial under microwave heating. The mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (Waters X-Bridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 12 mg of a solid (0.039 mmol, yield 20% for two steps).

Workup

temperatureheating
concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by preparative HPLC (Waters X-Bridge, gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record: ord-9cc89d3558264b7e9878887f2fbe6f7c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260441B2

Reaction notes

Loading…