Triethylamine → HCID 23447721, compound

HRID 1840282Notes

Reaction equation

HRID 1840282 reaction equation
C(N(CC)CC)C.C(Cl)(=O)OCC.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:27]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[N:26][N:25]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:24](=[O:40])[C:23]=2[C:41](O)=[O:42])=[CH:18][CH:17]=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:27]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[N:26][N:25]([CH2:36][CH:37]([CH3:38])[CH3:39])[C:24](=[O:40])[C:23]=2[CH2:41][OH:42])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 15518516HCID 15518516, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 23447721HCID 23447721, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (278.7 mg) and ethyl chlorocarbonate (298.9 mg) were added under ice cooling to a solution of 5,6-bis(4-methoxyphenyl)-4-carboxy-2-isobutyl-2H-pyridazin-3-one (750 mg, 1.84 mmol) in tetrahydrofuran (8 ml), followed by stirring for 1 hour. The reaction mixture was filtered. Under ice cooling, sodium borohydride (277.8 mg) was added to the filtrate, followed by stirring for 1 hour. The mixture was stirred further at room temperature for 2 hours. The reaction mixture was concentrated, to which a saturated aqueous solution of ammonium chloride was added. After the mixture was extracted with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, successively, and was the dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was separated and purified by chromatography on a silica gel column and then crystallized from ethyl acetate-hexane, whereby the title compound (383.0 mg, yield: 52.9%) was obtained as colorless needles.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionUnder ice cooling, sodium borohydride (277.8 mg) was added to the filtrate
  3. stirringby stirring for 1 hour
  4. stirringThe mixture was stirred further at room temperature for 2 hours
  5. concentrationThe reaction mixture was concentrated, to which a saturated aqueous solution of ammonium chloride
  6. additionwas added
  7. extractionAfter the mixture was extracted with ethyl acetate
  8. washthe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe residue was separated
  12. custompurified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-1b7512a68f8d49b3a27a828594195e7c
Source dataset
uspto-grants-2004_01
Patent number
US06680316B1

Reaction notes

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