Lawesson's reagent → HCID 56947465, compound

HRID 333099Notes

Reaction equation

HRID 333099 reaction equation
[CH3:1][CH:2]([CH3:22])/[CH:3]=[CH:4]/[C:5]([NH:7][CH2:8][CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([CH3:21])[CH:12]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>O1CCOCC1>[CH3:1][CH:2]([CH3:22])/[CH:3]=[CH:4]/[C:5](=[S:32])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([CH3:21])[CH:12]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66835575HCID 66835575, compound

Product 1

HCID 56947465HCID 56947465, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

(E)-4-Methyl-N-[2-[(2-methyl-4-quinolyl)amino]ethyl]pent-2-enamide (50 mg, 0.15 mmol) was dissolved in dioxane (2 ml), Lawesson's reagent (75 mg, 0.18 mmol) was added in one portion and the resulting mixture was stirred at 130° C. under microwave heating for 0.5 hrs. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 15 mg (0.047 mmol, 28.5%).

Workup

  1. temperatureheating for 0.5 hrs
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)
  4. customto yield 15 mg (0.047 mmol, 28.5%)

Sources & evidence

ORD record
ord-8c65f5bf5241465bbacb8a779a1fc5e9
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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