Cyclohexanecarboxylic acid → HCID 58415950, compound

Participants

Reaction Conditions

Reaction Steps

3-({[2-(4,4-difluoropiperidin-1-yl)-2-phenylethyl]amino}methyl)-1-methylquinolin-2(1H)-one (52 mg, 0.126 mmol), HATU (57.7 mg, 0.152 mmol), cyclohexanecarboxylic acid (0.019 ml, 0.152 mmol), and DIEA (0.026 ml, 0.152 mmol) were combined in DMF (1.5 ml) and the reaction heated at 50° C. for 0.75 hours. The mixture was purified directly by reversed-phase chromatography (15-95% ACN in water (with 0.5 ml/l NH4OH) over 20 min at 20 ml/min, 20×100 mm Phenomenex Gemini C18 column). Fractions containing desired material were concentrated in vacuo and repurified by reversed-phase chromatography (5-50% ACN (with 0.1% TFA) in water (with 0.1% TFA) over 20 min at 20 ml/min, 20×100 mm Phenomenex Gemini C18 column). Desired fractions were free-based via Phenomenex Strata X-C cartridge. HRMS [M+H] 1+ 522.2936. 1H NMR (400 MHz, CDCl3): δ 7.60-7.55 (m, 1 H), 7.53-7.49 (m, 1 H), 7.39 (d, J=8.52 Hz, 1 H), 7.35-7.28 (m, 4 H), 7.25-7.19 (m, 3 H), 4.50-4.35 (m, 2 H), 4.16-4.07 (m, 1 H), 3.88 (t, J=7.6 Hz, 1 H), 3.76 (s, 3 H), 3.31 (dd, J=7.38 Hz, 13.42 Hz, 1 H), 2.69-2.65 (m, 2 H), 2.53-2.43 (m, 2 H), 2.28-2.20 (m, 1 H), 2.01-1.88 (m, 4 H), 1.74-1.34 (m, 7 H), 1.25-1.05 (m, 3 H). 29.8 mg, 45%.

Provenance & Evidence