Potassium Carbonate → HCID 22340284, compound

HRID 585317Notes

Reaction equation

HRID 585317 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:11]=2)[N:6]=1)[CH3:3].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27](C(O)=O)=[CH:28]C=[CH:30][CH:31]=2)=[CH:22][CH:21]=1.CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])[O-].[K+].[K+]>Cl.CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:17]([C:16]([NH:15][C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][CH:9]=3)[N:6]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:14]=[CH:13]4)=[O:18])=[CH:30][CH:31]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27574184'-Chloro[1,1'-biphenyl]-2-carboxylic acidHCID 22340275HCID 22340275, compound

Product 1

HCID 22340284HCID 22340284, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

The N-[2-[(N,N-dimethylamino)methyl]-6-quinolinyl]acetamide (1.9 mg, 0.296 mmol) obtained in the above 1) was dissolved in concentrated hydrochloric acid (1.5 ml), and the solution was stirred at 110° C. for 2 hours. The solvent was distilled off under reduced pressure, an aqueous potassium carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue, 4′-chlorobiphenylcarboxylic acid (68.8 mg, 0.296 mmol) and dimethylaminopyridine (36.1 mg, 0.296 mmol) were dissolved in N,N-dimethylformamide (1.5 ml), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (56.6 mg, 0.296 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 16 hours. To the reaction solution was added an aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate), and crystallized from ethyl acetate-diisopropyl ether (1:5) to obtain the titled compound (60.6 mg) as a white powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionan aqueous potassium carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. temperaturecooling
  8. stirringthe mixture was stirred at room temperature for 16 hours
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe extract was washed with an aqueous saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate)
  14. customcrystallized from ethyl acetate-diisopropyl ether (1:5)

Sources & evidence

ORD record
ord-7162744d3f1a4ca8a855c95da817c65f
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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