Reaktion #68430

Reaktionsgleichung

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

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle