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

HRID 1058052ノート

反応式

HRID 1058052 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-306c5f8023034e3e8d6ee50acff5054c
出典データセット
uspto-grants-2003_02
特許番号
US06514977B1

反応ノート

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