Reaction #68430

Reaction equation

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

Solvents

CH2Cl2

Conditions

Workup

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

Procedure

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.

Source