Pyridine → HCID 68893750, compound

HRID 1786710Notes

Reaction equation

HRID 1786710 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11](O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:20](Cl)(=[O:24])C(Cl)=O.[Br:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29]>C1COCC1.CN(C=O)C.CN(C)C1C=CN=CC=1.C(#N)C.C(=O)(O)[O-].[Na+].C(N(CC)CC)C>[Br:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH:29][C:20]([CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:24]

Participants

11

Reactant 4

HCID 1049PyridineHCID 119922-BromoanilineHCID 65578Oxalyl chlorideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 68893750HCID 68893750, compoundYield 18%

Reagents, catalysts & solvents 6

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-(tert-butoxycarbonylamino)propionic acid (4.3 g) and pyridine (3.6 ml) in THF (40 ml) were added oxalyl chloride (3.0 ml) and DMF(3 drops) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. To the obtained reaction solution were added o-bromoaniline (2.6 g), triethylamine (6.3 ml) and a solution of 4-dimethylaminopyridine (0.37 g) in acetonitrile (50 ml) under ice-cooling, and the mixture was stirred at room temperature for 20 hours. The reaction mixture was diluted with saturated sodium bicarbonate solution (200 ml) and extracted with ethyl acetate (200 ml) twice. The extracted solutions were combined, washed with saturated brine, dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to give the title compound as white crystals (0.91 g, 18%).

Workup

  1. temperaturecooling
  2. customTo the obtained reaction solution
  3. stirringthe mixture was stirred at room temperature for 20 hours
  4. extractionextracted with ethyl acetate (200 ml) twice
  5. washwashed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-48f5b29454ff4ffa8f8e635f369abe30
Source dataset
uspto-grants-2009_03
Patent number
US07507753B2

Reaction notes

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