Hydrazine → 1-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-3,5-dimethylpiperazine

HRID 1167557Notes

Reaction equation

HRID 1167557 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[C:16]2SCS2)[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:21][CH:22]1[CH2:27][NH:26][CH2:25][CH:24]([CH3:28])[NH:23]1.[NH2:29][NH2:30]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:30][N:29]=[C:16]([N:26]3[CH2:25][CH:24]([CH3:28])[NH:23][CH:22]([CH3:21])[CH2:27]3)[C:9]=2[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 9321HydrazineHCID 660562,6-DimethylpiperazineHCID 155168911-(4-Chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone

Product 1

HCID 98421841-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-3,5-dimethylpiperazine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone (3.2 g, 0.01 mol; prepared as set forth in Step 1 of Example A-341) and 2,6-dimethylpiperazine (3.43 g, 0.03 mol) in 35 mL of toluene was heated at reflux for 12 hours. Toluene and excess 2,6-dimethylpiperazine were then removed under vacuum and the crude thiamide produced was used without purification. A solution of the crude thiamide and anhydrous hydrazine (0.65 g, 0.02 mol) in 40 mL of dry tetrahydrofuran was stirred at room temperature overnight. After the removal of tetrahydrofuran, the residue was stirred with a mixture of ethyl acetate and ammonium hydroxide for one hour. The precipitate was filtered and air dried to give 1.6 g of 1-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-3,5-dimethylpiperazine as a white solid (43% overall yield), mp: 236-238° C. Anal. Calc'd. for C20H22ClN5.0.25H2O: C, 64.51; H, 6.09; N, 18.81; Cl, 9.52. Found: C, 64.28; H, 5.85; N, 18.70; Cl, 9.67.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 12 hours
  4. customToluene and excess 2,6-dimethylpiperazine were then removed under vacuum
  5. customthe crude thiamide produced
  6. customwas used without purification
  7. customAfter the removal of tetrahydrofuran
  8. filtrationThe precipitate was filtered
  9. customair dried
  10. customto give

Sources & evidence

ORD record
ord-c6133ff0f7634b68a0aa6f61552b89c1
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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