Hydrochloric Acid → HCID 178430868, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 1-(4-methyl-1H-imidazol-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethylcarbamate (25.2 mg, 0.052 mmol) was dissolved in a minimum amount of ethyl acetate, and treated with hydrochloric acid (4 N in dioxane, 1.5 mL). The mixture was stirred under nitrogen for 3 days. After removal of the solvents, the crude mixture was treated with diethyl ether to give a precipitate which was filtered. The resulting solid was dissolved in dimethylformamide (1.0 mL), cooled to 0° C., and treated with carbonyl diimidazole (10.0 mg, 0.055 mmol, 1.1 equiv) and diisopropylethylamine (36.2 μL, 4.0 equiv). The reaction was stirred for 5 min at 0° C., warmed to room temperature, stirred for 10 min, and treated with 3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (13.0 mg, 0.055, 1.1 equiv). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue purified by column chromatography to afford 10.1 mg (38%, 2 steps). 1H-NMR (CD3OD, 500 MHz) δ 1.39-1.66 (m, 4H), 2.20 (s, 3H), 2.55 (s, 3H), 2.73-2.95 (m, 2H), 3.14-3.22 (m, 1H), 4.01-4.20 (m, 4H), 4.32-4.43 (m, 1H), 5.13-5.19 (m, 1H), 6.65 (s, 1H), 6.79 (d, J=7.6, 1H), 6.97 (dd, J=7.6, 7.3, 1H), 7.02 (s, 1H), 7.12 (d, J=7.3, 1H), 7.17 (dd, J=7.9, 7.3, 1H), 7.40 (s, 1H), 7.99 (s, 1H). Mass spec.: 513.3 (MH)+.

Provenance & Evidence