Trimethyl orthoformate → HCID 59277790, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N*4*-(3-Amino-phenyl)-4′-fluoro-biphenyl-3,4-diamine (Procedure O3, ˜5.1 mmol) in trimethylorthoformate (30 ml) was stirred and heated at 120° C. under N2 for 10 hours. The volatiles were removed in vacuo and the residue was taken up in EtOH (30 ml) and treated with c.HCl (2 ml), then stirred and heated at reflux for 3 hours. After cooling to RT, the mixture was concentrated to ˜2 ml, then diluted with H2O. NaHCO3 (sat) was added to give ˜pH7.5. The solid was taken up in CH2Cl2. The organic layer was dried and evaporated. The residue was purified by chromatography on silica (0%→1%→>2% 2M NH3-MeOH/CH2Cl2). The material was then triturated with Et2O to give the title compound (890 mg) as an off-white solid.

Provenance & Evidence