4-Methoxybenzylamine → HCID 71538599, compound

Participants

Reaction Steps

Using the conditions of General Procedure E for Amide Coupling in Parallel Mode, 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 2-methyl ester (which may be prepared as described for Intermediate 8; 100 mg, 0.21 mmol) was reacted with 4-methoxybenzylamine (available from Aldrich Chemical Company, Inc.; 85 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-4′-(4-methoxy-benzylcarbamoyl)-biphenyl-2-carboxylic acid (85 mg, 70%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.20 (br s, 1H), 9.08 (t, J=5.9 Hz, 1H), 8.48 (s, 1H), 8.38 (d, J=1.8 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.24 (dd, J=8.0, 1.8 Hz, 1H), 8.10 (dd, J=8.5, 2.0 Hz, 1H), 7.95 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.3 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.49 (d, J=8.3 Hz, 2H), 7.27 (d, J=8.5 Hz, 2H), 6.90 (d, J=8.5 Hz, 2H), 4.44 (d, J=6.0 Hz, 2H), 3.73 (s, 11H).

Provenance & Evidence