Potassium Carbonate → 2-(5-Amino-3-methylsulfanyl-[1,2,4]triazol-1-yl)-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone

HRID 1372134Notes

Reaction equation

HRID 1372134 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[C:5]([NH2:8])[NH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18]>CN(C=O)C>[NH2:8][C:5]1[N:6]([CH2:16][C:17]([N:19]2[CH2:20][CH2:21][N:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH2:23][CH2:24]2)=[O:18])[N:7]=[C:3]([S:2][CH3:1])[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 784713-(Methylthio)-1,2,4-triazol-5-amineHCID 40539571-(Chloroacetyl)-4-(4-chlorophenyl)piperazine

Product 1

HCID 210711172-(5-Amino-3-methylsulfanyl-[1,2,4]triazol-1-yl)-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Methylsulfanyl-2H-[1,2,4]triazol-3-ylamine (0.216 g, 1.7 mmol) was taken in dry DMF (15 ml) and dry potassium carbonate (800 mg) and KI (20 mg) was added to it and the reaction mixture stirred at room temperature for 1 h under nitrogen. 2-Chloro-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone (500 mg, 1.8 mmol) in DMF (5 ml) was then added to the mixture through a syringe. The reaction was then heated at 140° C. for 14 h cooled and then quenched with water and extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration afforded crude product that was purified by column chromatography (CHCl3/MeOH): 1H NMR (300 MHz, DMSO-d6): δ 7.24 (d, 2H), 6.98 (d, 2H), 6.24 (s, 2H), 4.84 (s, 2H), 3.57 (m, 4H), 3.21 (m, 2H), 3.13 (m, 2H), 2.37 (s, 3H).

Workup

  1. temperatureThe reaction was then heated at 140° C. for 14 h
  2. temperaturecooled
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialDrying of the organic layer with Na2SO4
  6. concentrationfollowed by concentration
  7. customafforded crude product that
  8. customwas purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-6d8493f802e440c9b39630e96dd44f3a
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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