Carbamic acid,n-[2-amino-5-(dimethylamino)-4-(trifluoromethyl)phenyl]-,1,1-dimethylethyl ester → 4-(3-Bromoacetyl-phenyl)-7-dimethylamino-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of (2-amino-5-dimethylamino-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J6) (0.32 g) and 3-oxo-3-[3-(2-bromo-1,1-dimethoxy-ethyl)-phenyl]-propionic acid tert-butyl ester (0.43 g) (Example K28) in toluene (3 mL) was heated to 100° C. for 2 h. The solvent was evaporated in vacuum and the crude product was purified by chromatography on silica gel using AcOEt/Hexan(1:3) as eluent. A solution of the purified material (0.57 g) in CH2Cl2/TFA (1:1, 7 mL) was stirred at 20° C. for 15 min and then evaporated. The residual oil was dissolved in AcOEt and the solution was washed with IN HCl and with brine, dried and evaporated to give crude 4-(3-bromoacetyl-phenyl)-7-dimethylamino-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (0.22 g) as light-brown solid.

Provenance & Evidence