Reacción #1929063

ord-11b227e362d247d6abe34ac0f6d8f0d4

Ecuación de reacción

N#CCC(=O)NCCCCCC(=O)O
6-(2-cyan-acetylamino)hexanoic acid
COc1ccc(C=O)cc1N(C)C
3-dimethylamino-4-methoxybenzaldehyde
C1CCNCC1
piperidine
COc1ccc(C=C(C#N)C(=O)NCCCCCC(=O)O)cc1N(C)C
6-[2-cyan-3-(3-dimethylamino-4-methoxy-phenyl)acryloylamino]hexanoic acid

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAfter evaporation of the reaction mixture the residue
  2. 2
    ExtracciónThe aqueous phase was extracted with ethyl acetate
  3. 3
    LavadoThe collected ethyl acetate phases were washed with NaCl-Solution
  4. 4
    Otrodried
  5. 5
    Otroevaporated
  6. 6
    OtroThe residue was chromatographed on SiO2 with ethyl acetate under low pressure
  7. 7
    OtroThe product was crystallized from little ethyl acetate

Procedimiento

3.96 g (20 mMol 6-(2-cyan-acetylamino)hexanoic acid was dissolved in 27 ml pyridine. 3.64 g (20 mMol) 3-dimethylamino-4-methoxybenzaldehyde and 0.6 mL piperidine were added to the solution and the reaction mixture was stirred for 20 hours. After evaporation of the reaction mixture the residue was solved in 150 ml ethyl acetate and 150 ml water and the pH was adjusted with pure acetic acid to 4.2. The aqueous phase was extracted with ethyl acetate. The collected ethyl acetate phases were washed with NaCl-Solution, dried and evaporated. The residue was chromatographed on SiO2 with ethyl acetate under low pressure. The product was crystallized from little ethyl acetate.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08946129B2uspto-grants-2015_02