Isobutyl chloroformate → 6-{3-[N-ethyl-N-(2-pyridyl)aminocarbonyl]propoxy}carbostyril

HRID 1903188Notes

Reaction equation

HRID 1903188 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]2)([OH:3])=O.C1[CH2:29][CH2:28][N:27]2[C:22](=[N:23][CH2:24][CH2:25][CH2:26]2)[CH2:21]C1.ClC(OCC(C)C)=O.C(NC1C=CC=CN=1)C>C(Cl)(Cl)Cl>[CH2:28]([N:27]([C:22]1[CH:21]=[CH:26][CH:25]=[CH:24][N:23]=1)[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]2)=[O:3])[CH3:29]

Participants

6

Reactant 4

HCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 118047452-(Ethylamino)pyridineHCID 128663424-((2-Oxo-1,2-dihydroquinolin-6-yl)oxy)butanoic acid

Product 1

HCID 128369556-{3-[N-ethyl-N-(2-pyridyl)aminocarbonyl]propoxy}carbostyril

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Into 300 ml of chloroform were added 9.9 g of 6-(3-carboxypropoxy)carbostyril and 6.5 ml of DBU. The outside of the reaction vessel containing the abovementioned mixture was ice-cooled and 5.7 ml of isobutyl chloroformate was added dropwise under stirring condition. After the addition operation, stirring was continued for 1 hour at a room temperature and 5.4 g of 2-ethylaminopyridine was added dropwise, then the reaction was continued for 5 hours under stirring condition. The reaction mixture was washed with a diluted NaHCO3 aqueous solution and water, and was concentrated. The residue thus obtained was treated by a silica-gel column chromatography (solvent used was a mixture of chloroform:methanol=20:1) and the elute thus obtained was concentrated then was recrystallized from methanol, to obtain 4.5 g of 6-{3-[N-ethyl-N-(2-pyridyl)aminocarbonyl]propoxy}carbostyril in the form of colorless needle-like crystals. Melting point: 148°-149° C.

Workup

  1. additionThe outside of the reaction vessel containing the abovementioned mixture
  2. temperaturecooled
  3. stirringAfter the addition operation, stirring
  4. waitthe reaction was continued for 5 hours
  5. stirringunder stirring condition
  6. washThe reaction mixture was washed with a diluted NaHCO3 aqueous solution and water
  7. concentrationwas concentrated
  8. customThe residue thus obtained
  9. additionwas treated by a silica-gel column chromatography (solvent
  10. washmethanol=20:1) and the elute thus
  11. customobtained
  12. concentrationwas concentrated
  13. customthen was recrystallized from methanol

Sources & evidence

ORD record
ord-f80d78a5cf8646e9b40df407ed380c35
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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