Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

To a suspension of 4-{5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyrimidin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (0.105 g, 0.201 mmol, 1 eq) in dioxane (1.5 mL) was added 4M HCl in dioxane (0.5 mL, 0.2 mmol, 10 eq) at 0° C. The reaction was allowed to warm to it and it was stirred overnight. After 18 h additional HCl (0.5 mL) was added and the reaction was stirred for 7 h. Solvents were removed under reduced pressure and the residue was treated with CH3CN. Solids were filtered off and washed with CH3CN to give the desired product as HCl salt (72 mg, 77%). HPLC-MS: (5-40% B in 8 min, 0.8 mL/min, 50° C.): tR=4.68 min, [M+H]+ m/z 424.2; 1H NMR (300 MHz, DMSO) δ 8.97 (s, 2H), 7.69 (s, 1H), 7.56 (d, J=8.3 Hz, 1H), 7.49 (s, 1H), 7.16 (d, J=8.5 Hz, 1H), 3.89 (s, 3H), 3.86 (s, 3H), 3.75 (m, 4H), 2.79 (m, 4H).

Provenance & Evidence