Ethyl Acetate → HCID 59515506, compound

HRID 1160228Notes

Reaction equation

HRID 1160228 reaction equation
[Cl:1][C:2]1[N:3]=NC(Cl)=[C:6]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.O.NN.C1N=C[N:27]([C:30]([N:32]2[CH:36]=[N:35]C=C2)=[O:31])C=1.C(OCC)(=O)C>C(O)C>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:6]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[C:36]2[N:32]([C:30](=[O:31])[NH:27][N:35]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 595155313,6-Dichloro-4-(4-chlorophenyl)-5-(pyridin-4-yl)pyridazine

Product 1

HCID 59515506HCID 59515506, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,6-dichloro-4-(4-chlorophenyl)-5-(pyridin-4-yl)pyridazine (0.69 g, 2.1 mmol) in ethanol (10 ml) was added hydrazine monohydrate (1.2 ml, 24.7 mmol). The reaction was stirred at 80° C. for 1 h. After this time, the reaction mixture was concentrated under reduced pressure. The crude product was then suspended in THF and CDI (1.36 g, 8.4 mmol) was added. The reaction turned to brownish clear solution, then to a suspension again. After stirring for 20 min, ethyl acetate was added. The resulting solution was washed with water and saturated NaCl. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with a gradient of 5%-10% methanol-dichloromethane to give 6-chloro-7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one as a brown sold (0.52 g) and 6-chloro-8-(4-chlorophenyl)-7-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one as light brown solid (0.27 g).

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure
  2. stirringAfter stirring for 20 min
  3. washThe resulting solution was washed with water and saturated NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel column chromatography
  8. washeluting with a gradient of 5%-10% methanol-dichloromethane

Sources & evidence

ORD record
ord-9fdbbd88c078440998fc84cb94897169
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

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