(2-Amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester → 4-[3-(4-Hydroxymethyl-thiazol-2-yl)-phenyl]-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J15) (0.145 g) and 3-oxo-3-[3-[4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-phenyl]-propionic acid tert.-butyl ester (Example K19) (0.23 g) in toluene (2 mL) was heated to 100° C. for 5 h. The mixture was cooled and evaporated in vacuum. A solution of the residue in a mixture of CH2Cl2 (2 mL) and TFA (2 mL) was stirred for 0.5 h at 20° C. The mixture was evaporated in vacuum, the residual oil was dissolved in AcOEt and the solution was washed with saturated NaHCO3 solution and with brine, dried over Na2SO4 and evaporated in vacuum. The residue was crystallized from CH2Cl2/hexane to give the title compound (0.04 g) as light-brown crystals.

Provenance & Evidence