Water → (+/-)-2-{4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazole-5-carbaldehyde

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Reaction Conditions

Reaction Steps

To a suspension of (±)-2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazole-5-carbonitrile (76 mg, 0.18 mmol) in toluene (anhydrous, 20 mL) was added diisobutylaluminium (1.4 M toluene solution) (0.65 mL, 0.97 mmol) at −78° C. under nitrogen. The mixture was stirred at −78° C. for 6 h. Ethyl acetate (1 mL) was then added followed by water (0.5 mL). The mixture was stirred at room temperature for 20 min. The mixture was then passed through a pad of celite and the filtrate was concentrated. The crude product was purified by prep. HPLC to yield the title compound (4 mg, 2.5%) as a brown solid. 1H NMR (300 MHz, CD3OD) δ 7.65 (1H, s), 7.57 (1H, s), 7.24–7.50 (5H, m), 6.26 (1H, d, J=7.6 Hz), 5.49 (1H, s), 4.96 (1H, m), 3.53–3.79 (2H, m), 2.62 (3H, s). LCMS (M+H)+ m/z 423 (t=1.79 min.).

Provenance & Evidence