4-Amino-1-methylpiperidine → HCID 86679845, 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-amino-1-methylpiperidine (available from Aldrich Chemical Company, Inc.; 71 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′-(1-methyl-piperidin-4-ylcarbamoyl)-biphenyl-2-carboxylic acid (135 mg, 116%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.20 (br s, 1H), 8.55 (d, J=7.5 Hz, 1H), 8.49 (s, 1H), 8.40 (d, J=1.8 Hz, 1H), 8.35 (d, J=2.0 Hz, 1H), 8.26 (dd, J=8.2, 1.9 Hz, 1H), 8.10 (dd, J=8.3, 2.0 Hz, 1H), 7.92 (d, J=8.3 Hz, 2H), 7.78 (d, J=8.3 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 4.01-4.10 (m, 1H), 3.45-3.51 (m, 2H), 3.05-3.18 (m, 2H), 2.78-2.81 (m, 2H), 2.54 (s, 3H), 2.02-2.10 (m, 2H).

Provenance & Evidence