Triethylamine → 1,6-Dihydro-6-oxo-1-[2-(3-quinolinylcarbonylamino)ethyl]-3-pyridinecarboxylic acid methyl ester

HRID 2379087Notes

Reaction equation

HRID 2379087 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH2:14])[CH:6]=1)=[O:4].[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]([C:25](O)=[O:26])[CH:16]=1.C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH:14][C:25]([C:17]2[CH:16]=[N:15][C:24]3[C:19]([CH:18]=2)=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:26])[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 80971Quinoline-3-carboxylic acidHCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 189578761,6-Dihydro-6-oxo-1-[2-(3-quinolinylcarbonylamino)ethyl]-3-pyridinecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (0.400 g, 2.0 mmol) was coupled with 3-quinolinecarboxylic acid (0.373 g, 2.2 mmol) in dichloromethane (35 ml) with triethylamine (1.40 ml, 10.0 mmol) and propylphosphoric acid anhydride (0.65 ml, added as a 0.65 ml ethyl acetate solution). After 17 hours, the solution was filtered through a pad of celite and the filtrate concentrated. Dichloromethane and aqueous sodium bicarbonate were added the layers separated. The aqueous layer was extracted with dichloromethane (2X) and the combined organic layers washed with aqueous sodium bicarbonate, brine, dried (Na2SO4), filtered, and concentrated. Recrystallisation from 1,2-dichloroethane gave the pure product, MP: 174°-175° C.

Workup

  1. filtrationthe solution was filtered through a pad of celite
  2. concentrationthe filtrate concentrated
  3. additionDichloromethane and aqueous sodium bicarbonate were added the layers
  4. customseparated
  5. extractionThe aqueous layer was extracted with dichloromethane (2X)
  6. washthe combined organic layers washed with aqueous sodium bicarbonate, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customRecrystallisation from 1,2-dichloroethane
  11. customgave the pure product, MP: 174°-175° C.

Sources & evidence

ORD record
ord-d5281cd30bbc4153ac390b9bb505001e
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

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