2-Dimethylaminopyridine → HCID 9823114, compound

HRID 585313Notes

Reaction equation

HRID 585313 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([NH:15][C:16](=[O:22])OC(C)(C)C)[CH:9]=[CH:8]2)[CH3:3].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:31](C(O)=O)=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:26][CH:25]=1.CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C>FC(F)(F)C(O)=O.CN(C)C=O.C(OCC)(=O)C>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:31]=[CH:32][C:33]([C:16]([NH:15][C:10]3[CH:9]=[CH:8][C:7]4[C:12](=[CH:13][CH:14]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:6]=4)[CH:11]=3)=[O:22])=[CH:34][CH:35]=2)=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27574184'-Chloro[1,1'-biphenyl]-2-carboxylic acidHCID 22340345HCID 22340345, compound

Product 1

HCID 9823114HCID 9823114, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl 6-[(N,N-dimethylamino)methyl]-2-naphthylcarbamate (237 mg, 0.789 mmol) obtained in Reference Example 1 was dissolved in trifluoroacetic acid (4 ml), the solution was stirred at room temperature for 1 hour, and the solvent was concentrated under reduced pressure. To the residue were added ethyl acetate and 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, 4′-chlorobiphenylcarboxylic acid (184 mg, 0.789 mmol) and dimethylaminopyridine (96.4 mg, 0.789 mmol) were dissolved in N,N-dimethylformamide (4 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (151 mg, 0.789 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temperature for 16 hours. To the reaction solution were added ethyl acetate and an aqueous potassium carbonate solution, the mixture was extracted, the organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by alumina column chromatography (developing solvent: ethyl acetate), and the insolubles were crystallized from a mixed solution of ethyl acetate and diisopropyl ether (1:5) to obtain the titled compound (207 mg) as a white powder.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. additionTo the residue were added ethyl acetate
  3. extractionan aqueous potassium carbonate solution, and the 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. temperatureunder ice-cooling
  8. stirringthe mixture was stirred at room temperature for 16 hours
  9. extractionan aqueous potassium carbonate solution, the mixture was extracted
  10. washthe organic layer was washed with an aqueous saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by alumina column chromatography (developing solvent: ethyl acetate)
  14. customthe insolubles were crystallized from a mixed solution of ethyl acetate and diisopropyl ether (1:5)

Sources & evidence

ORD record
ord-1db6e182721341f28ca4e2e236b5d311
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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