3,5-Dimethylpyrazole → HCID 57743136, compound

HRID 910132Notes

Reaction equation

HRID 910132 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.Cl[C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:15]([CH3:24])[N:14]=[N:13][C:12]=1[CH3:25].C(OCC)(=O)C>CN(C=O)C>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]2[C:11]([N:5]3[C:4]([CH3:3])=[CH:8][C:7]([CH3:9])=[N:6]3)=[C:12]([CH3:25])[N:13]=[N:14][C:15]=2[CH3:24])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 62103,5-DimethylpyrazoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 57743122HCID 57743122, compound

Product 1

HCID 57743136HCID 57743136, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

70 mg of sodium hydride (55% oil dispersion) was added to 1 ml of N,N-dimethylformamide (hereinafter, described as DMF) To this was added 0.17 g of 3,5-dimethylpyrazole, and the mixture was stirred for 1 hour at room temperature. To the resultant mixture was added a solution of 0.15 g of 4-chloro-5-(4-chlorophenyl)-3,6-dimethylpyridazine in 2 ml of DMF, and the mixture was stirred for 7 hours on an oil bath of 60° C. To the reaction mixture was added ethyl acetate and the mixture was washed with brine five times. The organic layer was dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. To 0.33 g of the resultant residue was added 50 ml of ethyl acetate, and washed with 50 ml of 1 mol/L hydrochloric acid and brine sequentially, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 0.21 g of the resultant residue was subjected to silica gel column chromatography, to obtain 0.12 g of 5-(4-chloro-phenyl)-4-(3,5-dimethyl-1-pyrazolyl)-3,6-dimethylpyridazine (hereinafter, described as compound (3) of the present invention).

Workup

  1. stirringthe mixture was stirred for 7 hours on an oil bath of 60° C
  2. washthe mixture was washed with brine five times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo 0.33 g of the resultant residue was added 50 ml of ethyl acetate
  6. washwashed with 50 ml of 1 mol/L hydrochloric acid and brine sequentially
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2877289a6814b4fb023ed2d963c7b84
Source dataset
uspto-grants-2011_09
Patent number
US08022073B2

Reaction notes

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