Reacción #2446058

ord-7c33c4dc3f37485184b755e6d5eb1034

Ecuación de reacción

O=C1c2cccc3c(Cl)ccc(c23)C(=O)N1CCSSCCN1C(=O)c2cccc3c(Cl)ccc(c23)C1=O
6-chloro-2-(2-{[2-(6-chloro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl]-disulphanyl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
CN(C)CCCN
N,N-dimethylpropane-1,3-diamine
CN(C)CCCNc1ccc2c3c(cccc13)C(=O)N(CCSSCCN1C(=O)c3cccc4c(NCCCN(C)C)ccc(c34)C1=O)C2=O
2,2′-(Disulphanediyldiethane-2,1-diyl)bis[6-{[3-(dimethylamino)propyl]-amino}-1H-benzo[de]isoquinoline-1,3(2H)-dione]

Condiciones de reacción

Temperatura
110°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe mixture is heated
  2. 2
    TemperaturaAfter cooling
  3. 3
    Otroa yellow precipitate is collected
  4. 4
    workup.ADDITION500 ml of a 1/1 ethanol/water mixture are added dropwise to the filtrate
  5. 5
    OtroThe yellow paste obtained
  6. 6
    Otrois isolated
  7. 7
    Otrotriturated with 200 ml of acetone
  8. 8
    OtroThe solids obtained
  9. 9
    Lavadoare washed with 300 ml of water
  10. 10
    Otrodried
  11. 11
    Otro4.5 g of yellow powder are recovered

Procedimiento

4 g of (6-chloro-2-(2-{[2-(6-chloro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl]-disulphanyl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione are suspended in 40 ml of N,N-dimethylpropane-1,3-diamine. The mixture is heated with stirring at 110° C. for 12 hours. After cooling, a yellow precipitate is collected, and 500 ml of a 1/1 ethanol/water mixture are added dropwise to the filtrate. The yellow paste obtained is isolated and triturated with 200 ml of acetone. The solids obtained are washed with 300 ml of water and dried. 4.5 g of yellow powder are recovered. The analyses show that the product is in accordance with the expected product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08685114B2uspto-grants-2014_04