Acetic Acid → HCID 70913292, compound

Participants

Reaction Steps

To a solution of 3-(benzylamino)-N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-2-(trifluoromethyl)benzamide (198 mg, 0.46 mmol) in DCE (5 ml) was added acetic acid (80 μl, 1.38 mmol) followed by acetaldehyde (129 μl, 2.31 mmol) after which the reaction was stirred at room temperature for 10 min. Then sodium triacetoxyborohydride (490 mg, 2.31 mmol) was added in one portion and the reaction was stirred at room temperature for 16 h. Further 4×130 uL treatments with acetaldehyde and 4×0.5 g sodium triacetoxyborohydride were performed over 3 days to completed the reaction. Water (100 ml) was then added to the reaction mixture and the aqueous phase was neutralized by the portionwise addition of NaHCO3. The aqueous phase was extracted with DCM (2×50 ml), then the combined organic phases washed with brine, dried (Na2SO4) and evaporated. The product was purified using FCC over a 5 g Isolute, eluting with 0-5% MeOH in DCM followed by purification via RP-HPLC to give the title compound as an off-white powder (76 mg, 34%). LC-MS 100%, m/z=458.3, 1H NMR (500 MHz, Chloroform-d) δ 11.70 (s, 1H), 7.42 (t, J=7.8 Hz, 1H), 7.36-7.27 (m, 5H), 7.24 (d, J=7.1 Hz, 1H), 7.12 (d, J=7.4 Hz, 1H), 7.03 (d, J=5.4 Hz, 1H), 5.90 (s, 1H), 4.50 (d, J=5.7 Hz, 2H), 4.05 (s, 2H), 2.96 (q, J=7.1 Hz, 2H), 2.36 (s, 3H), 2.15 (s, 3H), 0.89 (t, J=7.1 Hz, 3H).

Provenance & Evidence