Acetic Acid → HCID 67497638, compound

Participants

Reaction Steps

(2S)-2-amino-N-(3-chloro-5-(2-methylpyridin-4-yl)phenyl)-3-phenylpropanamide (32 mg, 87 μmol) was dissolved in trimethyl thoformate (1 ml) and acetic acid (0.25 ml, 4367 μmol). To this was added picolinaldehyde (94 mg, 875 mmol). After 30 min sodium cyanoborohydride (82 mg, 1312 μmol) dissolved in trimethyl orthoformate (1 ml). After 1 h the reaction mixture was poured onto 1N HCl and water was added, the mixture was concentrated under reduced pressure. The resulting crude solid was dissolved in AcOH/DMSO and purified on Phenomenex Geminni C18 HPLC 50 mm×250 mm running ACN/Water/0.1% TFA in a linear gradient. The fractions containing the desired product were combined and concentrated to afford (2S)—N-(3-chloro-5-(2-methylpyridin-4-yl)phenyl)-3-phenyl-2-(pyridin-2-ylmethylamino)propanamide (46) (30 mg, 75% yield). MS ESI (pos.) m/e: 457.1 (M+H). 1H NMR (500 MHz) (CDCl3) δ 10.13 (1H, s), 8.68 (1H, d, J=6.1 Hz), 8.50 (1H, d, J=5.4 Hz), 7.99 (1H, dt, J=1.2, 9.0 Hz), 7.88 (1H, s), 7.72-7.77 (3H, m), 7.47-7.53 (2H, m), 7.34 (1H, m), 7.16-7.24 (6H, m), 4.28-4.36 (3H, m), 3.30 (1H, dd, J=5.8, 13.9 Hz), 3.14 (1H, dd, J=7.8, 13.7 Hz).

Provenance & Evidence