Methanol → HCID 135681603, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-2-{4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}- -3H-benzimidazole-5-carboxylic acid ethyl ester (25 mg, 0,054 mmol) in methanol (2 mL) and acetic acid (1 mL) was added NaBH4 (10 mg, 0.27 mmol) at −20° C. The reaction mixture was stirred at −20° C. for 30 min. and quenched with isopropanol (5 drops). After removal of most solvent, the residue was extracted with EtOAc, washed with water and brine, dried over Na2SO4. After concentration, the crude product was purified by prep. HPLC to yield the title compound (18 mg, 62%). 1H NMR (300 MHz, CD3OD) δ 7.50 (1H, s), 7.48 (1H, s), 7.25–7.38 (4H, m), 7.22 (1H, s), 6.25 (1H, d, J=7.6 Hz), 4.89–4.94 (1H, m), 4.76 (2H, s), 3.51–3.62 (2H, m), 2.62 (3H, s). LCMS (M+H)+ m/z 425 (t=1.64 min.).

Provenance & Evidence