2-(4-Chlorophenyl)-2-oxoethyl thiocyanate → 4-(4'-{[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]amino}-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoic acid

Participants

Reaction Conditions

Reaction Steps

In a 8-mL screw-cap vial, a mixture of 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoic acid (60 mg, 0.20 mmol) and 2-(4-chlorophenyl)-2-oxoethyl thiocyanate (64 mg, 0.30 mmol) in 4 mL n-butanol was heated at 90° C. overnight. The solvent was removed under reduced pressure. The mixture was dissolved in 5 mL 1:4 MeOH/DMF and purified by reverse-phase HPLC to provide 6.8 mg (7%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 11.90 (br s, 1H), 10.50 (s, 1H), 7.75-8.00 (m, 10H), 7.50 (m, 3H), 3.30 (m, 2H), 1.05 (s, 6H); LC-MS m/z 491.2 (MH+), ret. time 3.83 min.

Provenance & Evidence