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

HRID 2230377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230377
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-986c85d2f4eb4f2e9d1467bb4b63b7e3
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423713B1

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