Reacción #46417

ord-eab120ff161a498aafa7ba098af8cad5

Ecuación de reacción

CCN(CC)CC
triethylamine
CCCCCCCCOC(=O)Cl
octyl chloroformate
CO.ClCCl
CH2Cl2 methanol
CN(C)CCN1C(=O)c2cccc3cc4cccc(N)c4c(c23)C1=O
11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione
CCCCCCCCOC(=O)Nc1cccc2cc3cccc4c3c(c12)C(=O)N(CCN(C)C)C4=O
desired product
Rendimiento 93.3%
CCCCCCCCOC(=O)Nc1cccc2cc3cccc4c3c(c12)C(=O)N(CCN(C)C)C4=O
octyl {2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}carbamate
Rendimiento 93.3%

Disolventes

Condiciones de reacción

Temperatura
20°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was then evaporated

Procedimiento

100 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.30 mmol) were dissolved in 6 ml dichloromethane. 85 μl (2 molar equivalents) of triethylamine and 127 mg (2 molar equivalents) of octyl chloroformate were respectively added. The reaction mixture was maintained at 20° C. for 3 hours. The solvent was then evaporated under reduce pressure and the residue was submitted to a flash chromatography on silica (eluent: CH2Cl2/methanol in a 95/5 volume ratio) to provide 137 mg (yield=85%) of the desired product (formula below) as an orange powder.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07741337B2uspto-grants-2010_06