Chloroacetyl chloride → HCID 66915947, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 mg 3-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethyl-1-quinolin-4-ylmethyl-imidazolidine-2,4-dione in 2 ml 1,2-dichloroethane in a process vial 0.08 ml ethyl-diisopropyl-amine and 27.2 mg chloroacetylchloride were added at 0° C. After stirring for 1 hour at 0° C. 119.4 mg 2,2,2-trifluoro-ethylamine were added. The resulting mixture was stirred for 1 hour at room temperature and then further 119.4 mg 2,2,2-trifluoro-ethylamine were added. The vial was sealed with a teflon septum and placed in the microwave cavity. The reaction mixture was stirred for 15 minutes at 100° C. by microwave-assisted heating (Emrys Optimizer, Personal Chemistry). After further 15 minutes stirring at 150° C. the solution was heated for 1 hour at 150° C. The solvent was removed under reduced pressure and the residue purified by preparative HPLC (C18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoracetic acid). Lyophilization of the solution yielded a white solid.

Provenance & Evidence