1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminothiocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 1841463Notes

Reaction equation

HRID 1841463 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:11][C:12](=[S:20])OC2C=CC=CC=2)[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([NH:11][C:12]([N:34]2[CH2:33][CH2:32][N:31]([C:25]3[CH:24]=[C:23]([O:22][CH3:21])[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=3)[CH2:36][CH2:35]2)=[S:20])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27362051-(3,5-Dimethoxyphenyl)piperazineHCID 54547361Phenyl N-(5,6-dimethyl-2-methoxypyrazin-3-yl)thiocarbamate

Product 1

HCID 539920091-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminothiocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-(5,6-dimethyl-2-methoxypyrazin-3-yl)thiocarbamate (200 mg, 0.69 mmol) and 1-(3,5-dimethoxyphenyl)piperazine (154 mg, 0.69 mmol) were dissolved in anhydrous tetrahydrofuran (25 ml) and thereto DBU (105 mg, 0.69 mmol) was added. The mixture was stirred at room temperature for 2 hours, concentrated under the reduced pressure to remove the solvent and purified by column chromatography to obtain the titled compound.

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove the solvent
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-7216931fd92d4965b0e2d0873b632525
Source dataset
uspto-grants-2004_01
Patent number
US06683184B2

Reaction notes

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