Lawesson's reagent → HCID 57940706, compound

HRID 1437296Notes

Reaction equation

HRID 1437296 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=O)=[N:10]2)=[CH:5][CH:4]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:38]2)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[S:38])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9951639HCID 9951639, compound

Product 1

HCID 57940706HCID 57940706, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-[1-(6-methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]-4-methylpiperazine (173 mg) obtained in Example 62 in toluene (10 mL), 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawson reagent, 222 mg) was added. The mixture was refluxed for 14 hours under heat. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate, water, and saturated brine, followed by drying over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was purified through silica gel thin-layer chromatography (chloroform-methanol), to thereby give the title compound as an amorphous product (61 mg, 33%).

Workup

  1. temperatureThe mixture was refluxed for 14 hours
  2. temperatureunder heat
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate, water, and saturated brine
  5. dry with materialby drying over sodium sulfate anhydrate
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified through silica gel thin-layer chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-d3aaf2ad03844c22ad1b400f8acb700d
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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