Acetic Anhydride → HCID 57585012, compound

Participants

Reaction Steps

6-(6-(3-aza-bicyclo[3.2.2]nonan-3-yl)pyrazin-2-yl)benzo[d]thiazol-2-amine was dissolved in 0.5 mL dry pyridine in a Biotage high recovery microwave vessel with a stirbar and treated with acetic anhydride (0.020 ml, 0.22 mmol). The vessel was swept with Ar, sealed and place into a 60° C. aluminum heat transfer block. The reaction was stirred for 4 h and cooled. The solution was treated with Si Carbonate (0.31 g, 0.22 mmol) (loading=0.69 mmol g−1), and the slurry was stirred at room temperature for 30 minutes. The slurry was filtered, and the silica was washed with dry pyridine (3 mL). The solvent was removed in vacuo to afford N-(6-(6-(3-aza-bicyclo[3.2.2]nonan-3-yl)pyrazin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.0024 g, 2.8% yield). 1H NMR (400 MHz, Pyr) δ ppm 1.22-1.41 (m, 8H) 1.76 (br. s., 2H) 2.06 (s, 3H) 3.57 (d, J=4.21 Hz, 4H) 7.85 (d, J=8.51 Hz, 1H) 8.12 (dd, J=8.41, 1.86 Hz, 1H) 8.13 (s, 1H) 8.48 (s, 1H) 8.71 (d, J=1.66 Hz, 1H) 13.58 (br. s., 1H). HPLC-MS: retention time=2.18 min (95%@215 nm; 97% @254 nm; m/z=394.2, calculated for C21H23N5OS+H+=394.2).

Provenance & Evidence