(1-Methyl-1H-pyrazol-5-yl)methanamine → HCID 71534656, 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 (1-methyl-1H-pyrazol-5-yl)methylamine (available from Aldrich Chemical Company, Inc.; 69 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-methyl-2H-pyrazol-3-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid (100 mg, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.23 (br s, 1H), 9.07 (t, J=5.6 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=8.4, 1.9 Hz, 1H), 7.94 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.32 (d, J=1.8 Hz, 1H), 6.19 (d, J=1.5 Hz, 1H), 4.55 (d, J=5.5 Hz, 2H), 3.84 (s, 3H).

Provenance & Evidence