3-Fluorobenzylamine → HCID 71538052, 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 3-fluorobenzylamine (available from Aldrich Chemical Company, Inc.; 78 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′-(3-fluoro-benzylcarbamoyl)-biphenyl-2-carboxylic acid (89 mg, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.17 (br s, 1H), 9.14 (t, J=6.0 Hz, 1H), 8.46 (s, 1H), 8.39 (d, J=1.8 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.24 (dd, J=8.0, 1.8 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.97 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.3 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.51 (d, J=8.3 Hz, 2H), 7.35-7.43 (m, 1H), 7.13-7.23 (m, 2H), 7.04-7.11 (m, 1H), 4.53 (d, J=6.0 Hz, 8H).

Provenance & Evidence