Hydrochloric Acid → HCID 57584917, compound

Participants

Reaction Steps

A dry 10 mL, round bottom flask was charged with N-(6-(6-chloro-5-((2-methoxyethoxy)methoxy)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0050 g, 0.012 mmol), a stirbar, and 1 mL dry TFE. To the stirring solution was added a 1 M solution of hydrochloric acid (0.037 ml, 0.037 mmol). The solution was transferred to a 5 mL, conical vial, purged with Ar, and sealed. The solution was irradiated using a Biotage microwave synthesizer for 5 minutes at 100° C. The cooled solution was concentrated in vacuo, and sonicated in 0.5 mL THF. The precipitate was collected using a glass frit under positive pressure nitrogen. The solids were washed with 0.5 mL dry THF, initially dried using a stream of nitrogen, and then at 60° C. and <1.0 mm Hg for 30 minutes to afford N-(6-(6-chloro-5-hydroxypyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0040 g). 1H NMR (400 MHz, DMF) 5 ppm 2.33 (s, 3H) 7.77 (dd, J=8.41, 1.86 Hz, 1H) 7.82 (d, J=2.25 Hz, 1H) 7.83 (d, J=8.61 Hz, 1H) 8.30 (d, J=2.15 Hz, 1H) 8.38 (d, J=1.76 Hz, 1H) 11.30 (br. s., 1H) 12.43 (br. s., 1H). 13C NMR (101 MHz, DMF) δ ppm 22.67 (s, 1 C) 120.44 (s, 1 C) 121.39 (s, 1 C) 122.26 (s, 1 C) 125.57 (s, 1 C) 132.27 (s, 1 C) 133.46 (s, 1 C) 137.13 (s, 1 C) 137.72 (s, 1 C) 137.88 (s, 1 C) 149.53 (s, 1 C) 150.58 (s, 1 C) 159.48 (s, 1 C) 169.92 (s, 1 C). 91741-17-1 HPLC-MS: retention time=1.56 min (96.0%@215 nm; >99% @254 nm; m/z=319.9, calculated for C14H10ClN3O2S+H+=320.0).

Provenance & Evidence