Acetic Acid → 1-(2-Quinoxalin-2-yl-ethyl)piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin4-yl)-amide

HRID 456600Notes

Reaction equation

HRID 456600 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15].[CH:22]([C:24]1[CH:33]=[N:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1)=[CH2:23].C(O)(=O)C.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14]([CH:16]1[CH2:21][CH2:20][N:19]([CH2:23][CH2:22][C:24]2[CH:33]=[N:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH2:18][CH2:17]1)=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 11231497Piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amideHCID 218034212-Ethenylquinoxaline

Product 1

HCID 102751461-(2-Quinoxalin-2-yl-ethyl)piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin4-yl)-amideYield 12.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of amine (1f) (0.403 g, 1.4 mmol), 2-vinyl-quinoxaline (b), (0.22 g, 1.4 mmol), acetic acid (0.1 ml) and ethanol (5.2 ml) was heated under reflux for 6 hours. The mixture was then made basic with aqueous sodium hydroxide and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with dichloromethane-methanol (99-1). After evaporation the residue was triturated with a small amount of ethyl acetate and crystallised. The solid was collected by filtration and dried to give the title compound (80 mg) mp.: 170° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with dichloromethane-methanol (99-1)
  8. customAfter evaporation the residue
  9. customwas triturated with a small amount of ethyl acetate
  10. customcrystallised
  11. filtrationThe solid was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-4d757dd362154ec9b15fc94b7f9cdbee
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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