Acetic Acid → HCID 25159784, compound

Participants

Reaction Steps

To a solution of 1-methyl-7-(((4-phenylpiperidin-4-yl)methoxy)methyl)-5-(trifluoromethyl)-1H-indazole (65 mg, 0.161 mmol) and sodium cyanoborohydride (20 mg, 0.322 mmol) in acetonitrile (1 mL) at room temperature was added formalin (50 μL). To this was added 1 drop of acetic acid. After 5 min, a second drop of acetic acid was added and the reaction stirred at room temperature for 15 min. The reaction was concentrated and loaded onto a strong cation exchange cartridge in methanol. The cartridge was washed with several volumes of methanol which were discarded. The product was eluted with 2 M ammonia in methanol and concentrated to give 19 mg (28%). 1H-NMR (CDCl3, 500 MHz) δ 7.99 (s, 1H), 7.95 (s, 1H), 7.31 (s, 1H), 7.23 (m, 4H), 7.17 (m, 1H), 4.66 (s, 2H), 3.90 (s, 3H), 3.47 (s, 2H), 2.51 (m, 2H), 2.18 (s, 3H), 2.05-2.25 (m, 4H), 1.91 (m, 2H); 13C-NMR (CDCl3, 126 MHz) δ 143.7, 139.5, 135.1, 133.8, 128.3, 127.2, 126.2, 124.74, 124.67 (q, J=272 Hz), 124.6, 122.6 (q, J=33 Hz), 121.3, 119.6 (q, J=3.8 Hz), 79.2, 70.6, 51.9, 46.2, 40.6, 38.2, 32.5. Mass spec.: 418.15 (MH)+. Accurate mass spec.: m/z 418.2119 [MH]+, Δ=3.1 ppm.

Provenance & Evidence