Triethylamine → HCID 16071132, compound

Participants

Reaction Steps

To a stirred solution of fluoro-6-bromo-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one (D46) (50 mg, 0.16 mmol), tetrahydro-4H-pyran-4-one (112 mg, 1.12 mmol) and triethylamine (49 mg, 0.48 mmol) in dichloromethane (5 ml) under argon was added portionwise sodium triacetoxyborohydride (240 mg, 1.12 mmol). The mixture was stirred at room temperature for 24 hrs, diluted with dichloromethane (5 ml) washed with 0.5N sodium hydroxide solution, dried (MgSO4) and concentrated in approx half volume before adding to a silica gel column which was subsequently eluted with 2-20% methanol in dichloromethane to afford 5-fluoro-6-bromo-1-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one. The isolated product was converted to the hydrochloride salt which was obtained as a colourless solid, 34 mg, 49%. MH+=398, and 400, 1H NMR (HCl salt) (DMSO-d6) δ: 1.24 (2H, m), 1.73 (3H, m), 1.89 (2H, m), 2.03 (2H, m), 2.83 (2H, m), 3.17 (2H, m), 3.58 (2H, m), 3.76 (1H, m), 4.59 (2H, m) 7.04 (1H, d, J=8 Hz), 7.94 (1H, d, J=5 Hz), 10.89 (1H, bs) and 11.32 (1H, s).

Provenance & Evidence