Stannous Chloride → HCID 68488874, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Nitro-1H-benzimidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]acetamide (60 mg, 0.17 mmol) (see Example 105) was dissolved in ethanol (1.44 mL) and tin(II) chloride (192 mg, is 0.85 mmol) was added. The reaction mixture was stirred at 70° C. for 16 h and then poured onto a mixture of ice and saturated aqueous NaHCO3 (20 mL). The basic solution was extracted with ethyl acetate (3×10 mL), washed with brine (10 mL), dried over anhydrous Na2SO4 and concentrated. The purification of the crude product was performed by preparative HPLC (XTerra C8 column 19×300 mm, 0.1 M NH4OAc/CH3CN). Product-containing fractions were pooled and lyophilised affording the title compound (11.3 mg, 20%). Calculated for C16H13F3N4O m/z: 334.10, found 335.09 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 5.07 (s, 2H), 5.24 (s, 2H), 6.37 (dd, J=7.6, 0.8 Hz, 1H), 6.64 (dd, J=8.0, 0.63 Hz, 1H), 6.90 (t, J=7.8 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.57 (t, J=8.0 Hz, 1H), 7.77 (m, 1H), 7.99 (s, 1H), 8.06 (s, 1H), 10.74 (s, 1H).

Provenance & Evidence