N,N-Dimethylethylenediamine → HCID 71534653, 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 N,N-dimethylethylenediamine (available from Aldrich Chemical Company, Inc.; 55 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′-(2-dimethylamino-ethylcarbamoyl)-biphenyl-2-carboxylic acid (81 mg, 73%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.73 (t, J=5.4 Hz, 1H), 8.47 (s, 1H), 8.41 (d, J=2.0 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.25 (dd, J=8.0, 1.8 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.93 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.52 (d, J=8.3 Hz, 2H), 3.63 (q, J=5.8 Hz, 2H), 3.22-3.27 (m, 2H), 2.84 (s, 6H).

Provenance & Evidence