1-(4-Aminopiperidin-1-yl)ethan-1-one → HCID 71534655, 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-acetylpiperidin-4-amine (available from Aldrich Chemical Company, Inc.; 88 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4′-(1-acetyl-piperidin-4-ylcarbamoyl)-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (5 mg, 4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.19 (br s, 1H), 8.45 (s, 1H), 8.33 (s, 3H), 8.19 (d, J=7.8 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.90 (d, J=8.0 Hz, 2H), 7.76 (d, J=8.3 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H), 4.35 (d, J=12.3 Hz, 1H), 4.05 (br s, 1H), 3.85 (d, J=13.3 Hz, 1H), 3.16 (t, J=11.8 Hz, 1H), 2.69 (d, J=13.3 Hz, 1H), 2.02 (s, 3H), 1.78-1.93 (m, 1H), 1.18-1.58 (m, 4H).

Provenance & Evidence