Hydrochloric Acid → HCID 178446890, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [1-bromo-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetonitrile (0.576 g, 1.20 mmol), sodium azide (0.393 g, 6.05 mmol) and ammonium chloride (0.33 g, 6.2 mmol) in DMF (10 mmol) was heated at 80° C. for three hours. After cooling to ambient temperature, the reaction mixture was poured into excess water and acidified with 2N hydrochloric acid. This was then extracted with ethyl acetate. The organic phase was washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by HPLC using 81% acetonitrile (0.1% formic acid) in water as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 58° C. for 16 hours yielded 1-{2-[5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-yl]-benzo[b]thiophen-3-yl}-pentan-1-one as a light yellow foam (0.312 g, 49.8%). Mass spectrum (+EI, [M+H]+) m/z 521/523. 1H NMR (500 MHz, DMSO-d6): δ16.6–17.3 (br, 1H), 8.24 (d, 1H, J=8.86 Hz),8.16–8.20 (m, 2H), 8.08–8.09 (m, 1H), 7.95–7.97 (m, 1H), 7.75–7.78 (m, 2H), 7.46–7.52 (m, 2H), 5.76 (s, 2H), 2.42 (t, 2H, J=7.26 Hz), 1.40–1.46 (m, 2H), 0.96–1.04 (m, 2H), 0.58 ppm (t, 3H, J=7.42 Hz). Elemental Analysis for C25H21BrN4O2S: Calcd: C, 57.59; H, 4.06; N, 10.74; Found: C, 57.42; H, 4.19; N, 10.59.

Provenance & Evidence