Dimethylformamide → HCID 13987705, compound

HRID 2231682Notes

Reaction equation

HRID 2231682 reaction equation
[Cl:1][C:2]1[C:3](=[O:28])[N:4]([CH:25]([CH3:27])[CH3:26])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][C:14]=1[CH2:22][CH2:23][CH3:24].C[N:30](C)C=O>>[Cl:1][C:2]1[C:3](=[O:28])[N:4]([CH:25]([CH3:27])[CH3:26])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:20])[NH2:30])=[CH:15][C:14]=1[CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 13987704HCID 13987704, compound

Product 1

HCID 13987705HCID 13987705, compound

Procedure

A mixture comprising 130 mg of Compound No. 41 i.e. 4 -chloro-5-[3-(2-n-propyl-4-carboxyphenoxy)propylamino]-2-i-propyl-3(2H)pyridazinone, 62 mg of N,N'-carbonyldiimidazole and 20 ml of N,N-dimethylformamide, was stirred at room temperature for 1 hour, and then ammonia gas was bubbled into the mixture for 10 minutes under cooling with ice. The system was closed and left to stand at room temperature for 2 hours. Then, the solvent was distilled off under reduced pressure. The residue was extracted with chloroform, and the chloroform layer was washed sequentially with an aqueous sodium hydroxide solution and a dilute hydrochloric acid aqueous solution, and dried over sodium sulfate. Then, chloroform was distilled off. The residue was treated with ethyl ether to obtain 20 mg of the above identified compound as a white powder.

Workup

  1. customammonia gas was bubbled into the mixture for 10 minutes
  2. temperatureunder cooling with ice
  3. customThe system was closed
  4. waitleft
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. extractionThe residue was extracted with chloroform
  7. washthe chloroform layer was washed sequentially with an aqueous sodium hydroxide solution
  8. dry with materiala dilute hydrochloric acid aqueous solution, and dried over sodium sulfate
  9. distillationThen, chloroform was distilled off
  10. additionThe residue was treated with ethyl ether
  11. customto obtain 20 mg of the

Sources & evidence

ORD record
ord-52edd5b9e90e4eeda861e1773a119266
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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