1,2-Dimethoxyethane → 1-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]thiocarbonyl]piperazine

HRID 352923Notes

Reaction equation

HRID 352923 reaction equation
C(COC)OC.[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([S:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]([C:28]3[N:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[CH:30][N:29]=3)=O)[CH2:22][CH2:21]1)(=[O:19])=[O:18])=[CH:11]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:49])=CC=1>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([S:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]([C:28]3[N:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[CH:30][N:29]=3)=[S:49])[CH2:22][CH2:21]1)(=[O:19])=[O:18])=[CH:11]2

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 87949Lawesson's reagentHCID 53268791-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]carbonyl]piperazine

Product 1

HCID 865920861-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]thiocarbonyl]piperazineYield 65.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a mixed solvent of dimethoxyethane (10 ml) and toluene (10 ml) was suspended 1-[(5-chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]carbonyl]piperazine (100 mg) at room temperature, followed by the addition of Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide, 42 mg). The resulting mixture was heated under reflux for 2 days. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by chromatography on a silica gel column (3→5% methanol—methylene chloride). 1N hydrochloric acid (in ethanol) was added to make acidic the purified product. After concentration, ethyl acetate was added. Yellow powder so precipitated was collected by filtration and dried, whereby the title compound (34 mg) was obtained.

Workup

  1. customat room temperature
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 2 days
  4. concentrationthe reaction mixture was concentrated
  5. customthe residue was purified by chromatography on a silica gel column (3→5% methanol—methylene chloride)
  6. addition1N hydrochloric acid (in ethanol) was added
  7. concentrationAfter concentration, ethyl acetate
  8. additionwas added
  9. customYellow powder so precipitated
  10. filtrationwas collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-9cde266921ff494799f5f380d0c1fd9f
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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