2-Aminothiazole → (3r,5r,7r)-N-(thiazol-2-yl)adamantane-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-aminothiazole (6.1 g, 61 mmol) in 250 mL of THF at 0° C. was added a solution of adamantane-1-carbonyl chloride (11 g, 55 mmol) in 25 mL of THF, followed by triethylamine (17 mL, 0.12 mol). The mixture was warmed to 65° C., stirred for 4 hours, and then allowed to cool to ambient temperature. The mixture was diluted with ethyl acetate and washed twice with water and brine. The aqueous washings were combined and extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 20-40% ethyl acetate/hexanes gradient) afforded 11 g (78%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.68-1.85 (m, 6H), 1.97 (d, J=3.1 Hz, 6H), 2.12 (s, 3H), 6.96 (d, J=3.7 Hz, 1H), 7.44 (d, J=3.4 Hz, 1H), 8.92 (s, 1H); MS (DCI/NH3) m/z 263 (M+H)+.

Provenance & Evidence