Tetrahydrofuran → HCID 178480034, compound

HRID 1890941Notes

Reaction equation

HRID 1890941 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[N:11][C:10]([NH:13][NH2:14])=[CH:9][CH:8]=2)[CH:4]=[N:3]1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[S:16].CCCCCC.C1COCC1>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:15]([SH:16])=[N:14][N:13]=3)[N:12]=2)[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 802641,1'-ThiocarbonyldiimidazoleHCID 580751723-Hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Product 1

HCID 178480034HCID 178480034, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

[6-(1-Methyl-1H-pyrazol-4-yl)-pyridazin-3-yl]-hydrazine (1.0 g, 5.3 mmol) and 1,1′-thiocarbonyldiimidazole (1.08 g, 6.1 mmol) were combined in DMF (10 mL) and heated at 50° C. for 2 h. After such time the mixture was allowed to cool to room temperature. Hexane (10 mL) was added followed by THF (4 mL), stirred for 10 mins then filtered and washed with THF (2 mL then 4 mL). Solid dried in vacuo to return 738 mg of 6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol as a yellow solid (60% yield).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthen filtered
  3. washwashed with THF (2 mL
  4. customSolid dried in vacuo

Sources & evidence

ORD record
ord-c7fd008ca4ed46aea2db9aef0ae8c665
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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