Ethyl Bromide → HCID 15859190, compound

HRID 583114Notes

Reaction equation

HRID 583114 reaction equation
[Cl:1][C:2]1[C:3](=[O:35])[NH:4][N:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)[CH:11]=1.[CH2:36](Br)[CH3:37].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:36]([N:4]1[C:3](=[O:35])[C:2]([Cl:1])=[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[CH2:23][CH2:22]3)[CH:11]=2)[CH:6]=[N:5]1)[CH3:37]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 21584189HCID 21584189, compound

Product 1

HCID 15859190HCID 15859190, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture comprising 500 mg of 4-chloro-5-[3-{2-(4-(4-fluorobenzyl)-piperazin-1-yl)-ethoxy}-4-methoxybenzylamino]-3(2H)-pyridazinone, 130 mg of ethyl bromide, 190 mg of potassium carbonate and 10 ml of 2-butanone, was refluxed under heating with stirring for 5 hours. Inorganic substances were filtered off, and then the solvent was distilled off under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with chloroform. The extract solution was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (eluent: chloroform/ethanol=19/1) to obtain 429 mg of the above-identified compound as a colorless transparent sticky substance.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. filtrationInorganic substances were filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionWater was added to the obtained residue
  6. extractionthe mixture was extracted with chloroform
  7. washThe extract solution was washed with water
  8. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  9. distillationThen, the solvent was distilled off
  10. customThe obtained residue was purified by silica gel column chromatography (eluent: chloroform/ethanol=19/1)

Sources & evidence

ORD record
ord-da7fd9c4c5164e53add67231ab4d0347
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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