3,5-Dimethylpyrazole → HCID 57743126, compound

HRID 910131Notes

Reaction equation

HRID 910131 reaction equation
[H-].[Na+].O1CCCC1.[CH3:8][C:9]1[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23](Cl)=[C:24]([Cl:29])[N:25]=[N:26][C:27]=2[CH3:28])=[CH:18][CH:17]=1>C(OCC)(=O)C>[Cl:29][C:24]1[N:25]=[N:26][C:27]([CH3:28])=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=2)[C:23]=1[N:10]1[C:9]([CH3:8])=[CH:13][C:12]([CH3:14])=[N:11]1

Participants

6

Reactant 4

HCID 62103,5-DimethylpyrazoleHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 57743115HCID 57743115, compound

Product 1

HCID 57743126HCID 57743126, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

29 mg of sodium hydride (55% oil dispersion) was added to tetrahydrofuran. Into this, a tetrahydrofuran solution of 3,5-dimethylpyrazole was added dropwise. The resultant mixture was added dropwise into 0.20 g of 5-(4-chloro-phenyl)-3,4-dichloro-6-methylpyridazine while cooling with ice. The mixture was stirred overnight at room temperature. To the reaction mixture was added ethyl acetate, and the mixture was washed with dilute hydrochloric acid water and brine sequentially. The organic layer was dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 0.27 g of the resultant residue was subjected to silica gel column chromatography, to obtain 50 mg of 3-chloro-5-(4-chlorophenyl)-4-(3,5-dimethyl-1-pyrazolyl)-6-m ethylpyridazine (hereinafter, described as compound (2) of the present invention) and 59 mg of 4-chloro-5-(4-chlorophenyl)-3-(3,5-dimethyl-1-pyrazolyl)-6-m ethylpyridazine.

Workup

  1. temperaturewhile cooling with ice
  2. washthe mixture was washed with dilute hydrochloric acid water and brine sequentially
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-207f6a9d1da648acb94afa344f73030c
Source dataset
uspto-grants-2011_09
Patent number
US08022073B2

Reaction notes

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