(2-Thienylmethyl)amine → HCID 71538600, 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 2-thiophenemethylamine (available from Aldrich Chemical Company, Inc.; 70 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′-[(thiophen-2-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid (47 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.24 (br s, 1H), 9.24 (t, J=5.9 Hz, 1H), 8.48 (s, 1H), 8.36 (dd, J=16.8, 2.0 Hz, 2H), 8.24 (dd, J=8.0, 2.0 Hz, 1H), 8.10 (dd, J=8.4, 2.1 Hz, 1H), 7.94 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.3 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.40 (dd, J=5.1, 1.1 Hz, 1H), 7.04 (d, J=2.5 Hz, 1H), 6.98 (dd, J=5.0, 3.5 Hz, 1H), 4.67 (d, J=5.8 Hz, 2H).

Provenance & Evidence