Acetic Acid → HCID 118566709, compound

Participants

Reaction Steps

To a stirred solution of 6-chloro-2-(1,2,3,6-tetrahydro-pyridin-4-yl)-quinoline-5-carboxylic acid (4,4-difluorocyclohexylmethyl)-amide (150.00 mg, 0.33 mmol, 1.00 eq) in 1,2-dichloroethane (5.00 mL, 33.33 V) was added acetone (0.05 mL, 0.66 mmol, 2.00 eq) and glacial acetic acid (0.04 mL, 0.66 mmol, 2.00 eq), then the reaction mixture was stirred at RT for 1 h and then cooled to 0° C. Sodium cyanoborohydride (43.54 mg, 0.66 mmol, 2.00 eq) was added and stirred at RT for 16 h. The solvent was removed and the crude product was purified by flash column chromatography using to afford 6-chloro-2-(1-isopropyl-1,2,3,6-tetrahydro-pyridin-4-yl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide (100.00 mg, 0.21 mmol, 62.5%, pale yellow solid). 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.83 (t, J=6.03 Hz, 1H), 8.00-7.96 (m, 3H), 7.76 (d, J=9.02 Hz, 1H), 6.91 (s, 1H), 3.27 (t, J=6.12 Hz, 4H), 2.70-2.65 (m, 4H), 2.04-2.02 (m, 2H), 1.86-1.74 (m, 5H), 1.33-1.17 (m, 2H), 1.05 (br s, 6H). m/z: 462.3 [M+H]+

Provenance & Evidence