Triethylamine → 4-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile

Participants

Reaction Steps

A solution of 2-(4-(3-amino-6-bromoquinolin-4-ylamino)phenyl)-2-methylpropanenitrile (Compound of Preparation D, 5 g, 13.1 mmol) and triethylamine (1.59 g, 15.7 mmol) in CH2Cl2 (120 mL) was added over 40 minutes to a solution of triphosgene (4.3 g, 14.4 mmol) in CH2Cl2 (80 mL) at 0° C. using ice-bath. The reaction mixture was stirred for 20 minutes at this temperature then was quenched with saturated aqueous NaHCO3, stirred for 5 minutes and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and solvent was evaporated to obtain the title compound. Yield: 3.2 g (60%); 1H NMR (DMSO-d6, 300 MHz): δ 11.835 (s, 1H), 8.783 (s, 1H), 7.908-7.938 (d, 1H, J=9 Hz), 7.810-7.838 (d, 2H, J=8.4 Hz), 7.665-7.694 (d, 2H, J=8.7 Hz), 7.613-7.650 (dd, 1H, J=9 Hz, 1.8 Hz), 6.949-6.955 (d, 1H, J=1.8 Hz), 1.609 (s, 6H); MS: m/z 406 (M+).

Provenance & Evidence