Acetyl chloride → HCID 86716121, compound

Participants

Reaction Steps

tert-Butyl 4-[(2,4-dichloro-3-phenylquinolin-6-yl)(hydroxy)pyridin-3-ylmethyl]piperidine-1-carboxylate (149 mg, 0.264 mmol, Example 91) was treated with TFA (1 mL) at room temperature for 1 hour and concentrated. A part of the residue (10 mg, 0.027 mmol), acetyl chloride (10 mg, 0.13 mmol), and Et3N (0.030 mL, 0.22 mmol) in CH2Cl2 (1 mL) was stirred overnight and concentrated. The residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA) to provide the title compound as a white solid. 1H NMR (400 MHz, MeOH-d4) δ 9.11 (s, 1H), 8.80 (t, J=7.33 Hz, 1H), 8.70 (d, J=5.56 Hz, 1H), 8.59-8.65 (m, 1H), 8.08-8.15 (m, 1H), 8.01-8.06 (m, 1H), 7.94-8.01 (m, 1H), 7.47-7.57 (m, 3H), 7.33 (t, J=6.57 Hz, 2H), 4.59 (d, J=13.14 Hz, 1H), 3.97 (d, J=13.14 Hz, 1H), 3.10-3.28 (m, 2H), 2.63-2.76 (m, 1H), 1.37-1.67 (m, 4H); MS m/e 506.1 [M+H]+.

Provenance & Evidence