Formaldehyde → HCID 86716119, compound

Participants

Reaction Steps

To a mixture of (2,4-dichloro-3-phenylquinolin-6-yl)(piperidin-3-yl)pyridin-3-ylmethanol•TFA (15 mg, 0.022 mmol, Example 93), 37% formaldehyde in water (0.010 mL, 0.13 mmol) and MeOH (1 mL) was added NaBH3CN (4.0 mg, 0.064 mmol). The mixture 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 8.95 (s, 1H), 8.54-8.68 (m, 2H), 8.41 (d, J=7.58 Hz, 1H), 7.96-8.13 (m, 2H), 7.72 (dd, J=5.14, 7.58 Hz, 1H), 7.53 (d, J=7.09 Hz, 3H), 7.33 (d, J=6.85 Hz, 2H), 3.48-3.64 (m, 1H), 3.10-3.21 (m, 1H), 2.96-3.10 (m, 1H), 2.83-2.97 (m, 1H), 2.80 (s, 3H), 2.66 (s, 1H), 2.01-2.13 (m, 1H), 1.82-2.01 (m, 1H), 1.54-1.82 (m, 2H); MS m/e 478.0 [M+H]+.

Provenance & Evidence