Tetrahydrofuran → HCID 66843921, compound

HRID 254832Notes

Reaction equation

HRID 254832 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21](=O)[CH2:22][C:23](=O)[C:24]([CH3:27])([CH3:26])[CH3:25])[C:9]=2[CH3:30])=[CH:4][CH:3]=1.O.[NH2:32][NH2:33].C1COCC1>CCO>[C:24]([C:23]1[NH:33][N:32]=[C:21]([C:10]2[C:9]([CH3:30])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=2)[CH:22]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 66844585HCID 66844585, compound

Product 1

HCID 66843921HCID 66843921, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 1-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-4,4-dimethylpentane-1,3-dione (555 mg, 1.20 mmol) (B) in EtOH (5.5 mL) was added hydrazine monohydrate (0.12 g, 2.4 mmol). The reaction mixture was refluxed at 90° C. for 6 hours. After cooled down to room temperature, the resulting suspension was dissolved by addition of THF (15 mL) and further purified by prep HPLC to provide 350 mg (0.761 mmol, 63%) of the title compound.

Workup

  1. temperatureAfter cooled down to room temperature
  2. customfurther purified by prep HPLC

Sources & evidence

ORD record
ord-5b3863e7aa274299a1f29a3194407642
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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