Hydrochloric Acid → HCID 178446889, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of {1-bromo-6-[3-(3-methyl-butyryl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetonitrile (1.01 g, 2.11 mmol), sodium azide (0.687 g, 10.6 mmol) and ammonium chloride (0.570 g, 10.7 mmol) in DMF (10 mmol) was heated at 80° C. for two 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. Drying in vacuo at 78° C. for 12 hours yielded 1-{2-[5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-yl]-benzo[b]thiophen-3-yl}-3-methyl-butan-1-one as a yellow foam (0.602 g, 75%). Mass spectrum (+EI, [M+H]+) m/z 521/523. 1H NMR (500 MHz, DMSO-d6): δ16.7–17.2 (br, 1H), 8.24 (d, 1H, J=9.01 Hz), 8.16–8.19 (m, 2H), 8.08–8.10 (m, 1H), 7.95–7.97 (m, 1H), 7.75–7.79 (m, 2H), 7.46–7.52 (m, 2H), 5.77 (s, 2H), 2.32 (d, 2H, J=6.72 Hz), 1.95–2.02 (m, 1H), 0.65 ppm (d, 6H, J=6.57 Hz). Elemental Analysis for C25H21BrN4O2S: Calcd: C, 57.59; H, 4.06; N, 10.74; Found: C, 57.37; H, 4.12; N, 10.48.

Provenance & Evidence