Reacción #2358551

ord-3b8f9ee181bd412aaeb0eee78b901aca

Ecuación de reacción

Cl
HCl
O=C(Cl)OCc1ccccc1
Cbz-Cl
CCOCOc1cc(OCc2ccccc2)c(-c2n[nH]c(=O)n2-c2ccc3c(ccn3C)c2)cc1C(C)C
3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-1H-1,2,4-triazol-5(4H)-one
CCN(C(C)C)C(C)C
DIPEA
CCOCOc1cc(OCc2ccccc2)c(-c2nn(C(=O)OCc3ccccc3)c(=O)n2-c2ccc3c(ccn3C)c2)cc1C(C)C
benzyl 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxylate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoWashed with water
  2. 2
    Extracciónextracted with dichloromethane and solvent
  3. 3
    Otrowas removed
  4. 4
    OtroThe crude reaction mixture
  5. 5
    Otrowas carried over to the next reaction without further purification
  6. 6
    Temperaturaheated it up to 65° C

Procedimiento

Cbz-Cl was added to the solution of 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-1H-1,2,4-triazol-5(4H)-one and DIPEA in dichloromethane and reaction solution was stirred for 2 h at room temperature. Washed with water and extracted with dichloromethane and solvent was removed. The crude reaction mixture was carried over to the next reaction without further purification. The reaction mixture was diluted by methanol and treated with concentrated HCl and heated it up to 65° C. Column chromatogram produced the desired benzyl 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxylate.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09120745B2uspto-grants-2015_09