Reacción #68430

Ecuación de reacción

6-amino-N-(3,4-difluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

Compound 182

6-amino-N-(3,4-difluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

chloroethyl isocyanate

→

title compound

N-(3,4-Difluorobenzyl)-6-(4,5-dihydrooxazol-2-ylamino)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed
2. 2
   workup.ADDITIONTo the residue was added H2O
3. 3
   Temperaturathe mixture was heated at 80° C. for 3 h
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   Lavadowashed with aqueous K2CO3 and brine
6. 6
   Secadodried over Na2SO4
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

Procedimiento

To a solution of 6-amino-N-(3,4-difluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 182, 48 mg, 0.11 mmol) in CH2Cl2 (1 ml) was added chloroethyl isocyanate (10 μl, 0.12 mmol). The reaction was stirred at room temperature for 16 h, and the solvent was removed. To the residue was added H2O and the mixture was heated at 80° C. for 3 h, diluted with EtOAc, washed with aqueous K2CO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound.

Fuente