Hydrochloric Acid → HCID 57585094, compound

Participants

Reaction Steps

A 5 mL, conical microwave vessel was charged with N-(6-(5-((2-methoxyethoxy)methoxy)-6-(trifluoromethyl)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0137 g, 0.031 mmol), 1M HCl (0.093 ml, 0.093 mmol) and 1.5 mL TFE. The vessel was flushed with nitrogen, sealed, and irradiated to 100° C. using a Biotage initiator microwave for 10 minutes. The solution was concentrated in vacuo, and dried at <1.0 mm Hg for 1 h. The residue was treated with 0.5 mL EtOH, briefly sonicated, and set at room temperature for 1 h. The solids were collected using a 0.22 μm PTFE filter under positive pressure nitrogen, and washed with 0.5 mL EtOH. The precipitate was heated into 2 mL TFE, filtered through a 0.22 μm PTFE filter, and concentrated in vacuo. The solids were then dried at 60° C. and <0.5 mm Hg for 1 h to afford N-(6-(5-hydroxy-6-(trifluoromethyl)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0068 g, 62% yield). 1H NMR (400 MHz, THF) δ ppm 2.22 (s, 3H) 7.53 (d, J=1.37 Hz, 1H) 7.68 (dd, J=8.46, 1.91 Hz, 1H) 7.77 (dd, J=8.41, 0.49 Hz, 1H) 8.18 (d, J=1.76 Hz, 1H) 8.47 (d, J=1.66 Hz, 1H) 9.68 (br. s., 1H) 11.36 (br. s., 1H). 19F NMR (377 MHz, THF) δ ppm −65.58 (s, 3 F). HPLC-MS: retention time=1.78 min (97.7%@215 nm; 97.8% @254 nm; m/z=354.0, calculated for C15H10F3N3O2S+H+=354.0).

Provenance & Evidence