Acetaldehyde → HCID 54691307, compound

Participants

Reaction Steps

A mixture of 2-chloro-4-hydroxy-3-{4-[(4-hydroxypiperidin-4-yl)methoxy]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile TFA salt (40 mg, 0.073 mmol), acetaldehyde (0.006 mL, 0.110 mmol), and MS-CNBH3 (88 mg, 0.110 mmol, 1.25 mmol/g loading) in a 1:1 mixture of DMSO/MeOH (1 mL) containing 2% v/v AcOH was shaken in a 1 dram vial at rt for 18 h. The mixture was then filtered and purified by RP-HPLC to give the title compound. MS (ESI) m/e 460 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.24 (t, J=7.29 Hz, 3H), 1.83 (m, 2H), 1.98 (m, 2H), 3.15 (m, 4H), 3.32 (d, J=7.29 Hz, 2H), 3.87 (s, 2H), 5.22 (s, 1H), 6.92 (d, J=8.82 Hz, 2H), 7.20 (d, J=8.82 Hz, 2H), 8.91 (s, 1H), 10.77 (s, 1H).

Provenance & Evidence