acetyl azide

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]benzonitrile (100 mg, 0.23 mmol) in dry toluene is added acetic azide (34 mg, 0.46 mmol) and K2CO3 (158 mg, 0.115 mmol) under nitrogen. The reaction mixture is heated to 110° C. for 12 h under nitrogen after which it is concentrated under vacuum. The solid residue is purified by Preparative HPLC to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.21-8.19 (d, J=7.7 Hz, 1H), 8.03-7.98 (m, 2H), 7.73-7.69 (m, 1H), 7.64-7.56 (m, 3H), 6.92-6.90 (d, J=7.8 Hz, 1H), 4.91 (s, 2H), 3.93 (m, 2H),3.75-3.67 (m, 4H), 3.62-3.61 (m, 2H), 2.37 (s, 3H). MS (ESI+): 491.0. HPLC (max plot) 98.76%; Rt 2.96 min. is concentrated under vacuum The solid residue is purified by Preparative HPLC