Chloroacetaldehyde → HCID 11386975, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl)phenyl)-5-phenylpyridine-3-carboximidamide (3-2, 0.030 g, 0.059 mmol) in Dioxane (1.5 mL) was added chloroacetaldehyde (50% solution in H2O, 0.019 mL, 0.119 mmol) followed by sodium carbonate (0.016 mg, 0.149 mmol). The reaction was heated to 110° C. for 1 hr. The mixture was cooled and partitioned between saturated aqueous sodium bicarbonate and CH2Cl2 and extracted 3×. The combined organics were dried (anhd. Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (6-8% MeOH in CH2Cl2). 1H-NMR (500 MHz, d6 DMSO) δ 12.83 (s, 1H), 12.31 (s, 1H), 9.21 (d, J=1.95, 1H), 8.74 (s, 1H), 8.30 (d, J=2.2, 1H), 7.08-7.42 (m, 12H), 6.97 (bs, 1H), 3.61 (bs, 2H), 3.50 (bs, 1H), 3.13 (bs, 2H), 2.87 (bs, 2H), 1.98 (bs, 2H), 1.84 (bs 2H). HRMS m/z (M+H) Calcd: 529.2511, found: 529.2532.

Provenance & Evidence