Triethylamine → HCID 53307541, compound

Participants

Reaction Steps

To a solution of 4-[(6-chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (A) (0.15 g, 0.38 mmol) in 3.5 mL ethyl acetate and a few drops of methanol to increase solubility was added triethylamine (0.053 mL, 0.38 mmol) and palladium on carbon (10 mol %). The reaction mixture was placed under a H2 (g) atmosphere with a balloon for 18 h. The reaction mixture was filtered through Celite, washed with excess methanol, and concentrated. The resulting residue was subjected to purification via reverse phase HPLC to afford the title compound that gave a mass ion (ES+) of 362.1866 for M+H+. 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.49 (dd, J=1.3, 4.8 Hz, 1H), 8.27 (d, J=7.7 Hz, 1H), 8.17 (s, 1H), 8.15 (dd J=0.7, 8.6 Hz, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.78-7.74 (m, 1H), 7.63-7.52 (m, 1H), 7.44-7.42 (m, 1H), 7.19 (dd, J=4.9, 7.9 Hz, HA 4.51 (s, 2H), 3.93-3.84 (m, 1H), 3.62-3.54 (m, 1H), 3.36 (d, J=4.2, 1H), 2.17-2.12 (m, 2H) 1.82-1.79 (m, 2H), 1.52-1.34 (m, 4H).

Provenance & Evidence