Dipropylamine → HCID 13853897, compound

HRID 2372347Notes

Reaction equation

HRID 2372347 reaction equation
[Cl:1][C:2]1[C:3](=[O:22])[N:4]([CH:19]([CH3:21])[CH3:20])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][CH:11]=1.[CH2:23]([NH:26][CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25]>CN(C)C=O>[Cl:1][C:2]1[C:3](=[O:22])[N:4]([CH:19]([CH3:21])[CH3:20])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([N:26]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][CH3:25])=[O:18])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 19903188HCID 19903188, compound

Product 1

HCID 13853897HCID 13853897, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 322 mg of 4-chloro-5-(4-carboxy-benzylamino)-2-i-propyl-3(2H)pyridazinone obtained from 2-i-propyl-4,5-dichloro-3(2H)pyrisazinone and 4-carbonxybenzylamine, 194 mg of N,N'-carbonyldiimidazole and 5 ml of dimethylformamide, was stirred at room temperature for one hour. A solution obtained by dissolving 100 mg of di-n-propylamine in 1 ml of dimethylformamide was added thereto, and the mixture was stirred at the same temperature overnight. The solvent was distilled off under reduced pressure, and the pale yellow oily substance thereby obtained was extracted with chloroform. The extract was washed successively with diluted hydrochloric acid, water, a 5% sodium hydroxide aqueous solution and a saturated sodium chloride aqueous solution, and dried over sodium sulfate, and then the solvent was distilled off to obtain a pale yellow oily substance. This substance was subjected to silica gel column chromatography and eluted with benzene:ethyl acetate (2:5, v/v). The colorless viscous oily substance thereby obtained was crystallized from ether-n-hexane to obtain 108 mg of the above identified compound having a melting point of from 78° to 81° C. as colorless crystals.

Workup

  1. customobtained from 2-i-propyl-4,5-dichloro-3(2H)pyrisazinone
  2. customA solution obtained
  3. additionwas added
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe pale yellow oily substance thereby obtained
  6. extractionwas extracted with chloroform
  7. washThe extract was washed successively with diluted hydrochloric acid, water
  8. dry with materiala 5% sodium hydroxide aqueous solution and a saturated sodium chloride aqueous solution, and dried over sodium sulfate
  9. distillationthe solvent was distilled off
  10. customto obtain a pale yellow oily substance
  11. washeluted with benzene:ethyl acetate (2:5
  12. customThe colorless viscous oily substance thereby obtained
  13. customwas crystallized from ether-n-hexane
  14. customto obtain 108 mg of the
  15. customof from 78° to 81° C.

Sources & evidence

ORD record
ord-b17e8a57fdbf4672b6ace2fd65c5861f
Source dataset
uspto-grants-1992_03
Patent number
US05098900

Reaction notes

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