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Potassium Carbonate → 8-Chloro-7-(4-chlorophenyl)-2-(pyrazin-2-ylmethyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

HRID 2224273
Notes
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Reaction equation

HRID 2224273 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[N:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[N:16]([CH2:26][C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)[N:17]=2)[N:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 170169Pyrazine, 2-(chloromethyl)-HCID 597166868-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

Product 1

HCID 597167678-Chloro-7-(4-chlorophenyl)-2-(pyrazin-2-ylmethyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-oneYield 74%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one (0.62 g, 2.21 mmol), prepared as described in Example 354, in DMF (10 mL) at RT was added K2CO3 (0.61 g, 4.4 mmol) and 2-(chloromethyl)pyrazine (0.83 g). The reaction mixture was heated at 50° C. for 2 h. After this time, the mixture was diluted with EtOAc (150 mL). The resultant solution was washed with water and saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with hexanes:EtOAc 1:2 to afford 0.61 g of the title compound, 8-chloro-7-(4-chlorophenyl)-2-(pyrazin-2-ylmethyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one as a yellow solid. HPLC RT: 2.86 min; MS, M+H=373; 1H NMR (CDCl3): δ 8.64 (d, 1H), 8.54 (m, 2H), 8.11 (s, 1H), 7.54-7.49 (m, 4H), 5.48 (s, 2H).

Workup

  1. washThe resultant solution was washed with water and saturated aqueous NaCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with hexanes:EtOAc 1:2

Sources & evidence

ORD record
ord-f6bbeb0c13c0403c86e627b21c6ed396
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07378418B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes