Ethanol → HCID 68969554, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-cyano-2,6-dimethyl-N-((R)-3-{4-[(4-methyl-pyridin-3-ylmethyl)-phenyl-amino]-piperidin-1-yl}-butyl)-benzamide (0.21 g, 0.41 mmol) in EtOH (10 mL) was added 3N NaOH (5 mL) and the resulting colourless solution was stirred at 100° C. for 18 h. The EtOH was removed in vacuo and the pH adjusted to ˜5 before dry loading onto silica gel. Purification by column chromatography on silica gel (8:1:1, CH3CN/MeOH/NH4OH) afforded 3,5-dimethyl-N-((R)-3-{4-[(4-methyl-pyridin-3-ylmethyl)-phenyl-amino]-piperidin-1-yl}-butyl)-terephthalamic acid (0.23 g, 100%) as a white solid. 1H NMR (CD3OD) δ 1.43 (d, 3H, J=8 Hz), 1.91 (m, 1H), 2.14 (m, 3H), 2.22 (m, 1H), 2.32 (s, 6H), 2.41 (s, 2H), 3.34 (s, 5H), 3.45 (m, 4H), 3.53 (m, 1H), 4.20 (m, 1H), 4.48 (s, 2H), 6.79 (m, 3H), 7.19 (m, 3H), 7.66 (m, 2H), 8.23 (m, 2H).

Provenance & Evidence