4-Chloro-3-methoxybenzoic acid → 4-Amino-5-chloro-6-ethoxy-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide

Participants

Reaction Steps

According to the same procedure described in Example 16 and starting with 4-amino-5-chloro-6-ethoxypicolinic acid (prepared according to the reported preparation in J. Med. Chem. 2006, 49, 4455) instead of 4-chloro-3-methoxybenzoic acid and the compound prepared in Example 214 instead of the compound prepared in Example 9, the title compound having the following physical data was obtained. 1H NMR (DMSO-d6): δ 8.61 (d, J=4.7 Hz, 1H), 8.33 (t, J=6.4 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 7.94 (td, J=1.7, 7.7 Hz, 2H), 7.78 (s, 1H), 7.47 (ddd, J=1.1, 4.8, 7.5 Hz, 1H), 7.09 (s, 1H), 6.50 (s, 1H), 4.45 (q, J=7.0 Hz, 2H), 3.73 (s, 2H), 3.16 (t, J=6.5 Hz, 2H), 2.85-2.88 (m, 2H), 1.97 (t, J=10.7 Hz, 2H), 1.60-1.63 (m, 2H), 1.50-1.55 (m, 1H), 1.31 (t, J=7.0 Hz, 3H), 1.15-1.24 (m, 2H);

Provenance & Evidence