Ethyl Bromide → HCID 15859189, compound

HRID 583113Notes

Reaction equation

HRID 583113 reaction equation
[Cl:1][C:2]1[C:3](=[O:30])[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][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH:28]=O)[CH2:24][CH2:23]2)[CH:11]=1.[OH-].[K+].[C:33](=O)([O-])[O-].[K+].[K+].C(Br)C>O.C(O)C>[Cl:1][C:2]1[C:3](=[O:30])[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][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH3:33])[CH2:24][CH2:23]2)[CH:11]=1

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 158591884-Chloro-5-[3-{3-(4-formylpiperazin-1-yl)-propoxy}-4-methoxybenzylamino]-3(2H)-pyridazinone

Product 1

HCID 15859189HCID 15859189, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture comprising 1.0 g of 4-chloro-5-[3-{3-(4-formylpiperazin-1-yl)-propoxy}-4-methoxybenzylamino]-3(2H)-pyridazinone, 0.62 g of potassium hydroxide, 7 ml of ethanol and 7 ml of water, was refluxed under heating with stirring for 3.5 hours, and then 0.32 g of potassium carbonate and 570 mg of ethyl bromide were added thereto. The mixture was stirred at 60° C. for 4 hours. The solvent was distilled off under reduced pressure, and water was added to the obtained residue. 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 to obtain 0.50 g of the above-identified compound as slightly brown solid.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. stirringThe mixture was stirred at 60° C. for 4 hours
  4. distillationThe solvent was distilled off under reduced pressure, and water
  5. additionwas 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

Sources & evidence

ORD record
ord-ea2f46f2ca024c838c13f6481ed24e53
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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