Triethylamine → (R)-N-(6-fluoro-1H-indazol-3-yl)-4H-1'-azaspiro[oxazole-5,3'-bicyclo[2.2.2]octan]-2-amine

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To 6-fluoro-3-isothiocyanato-1H-indazole (0.20 g, 1.04 mmol) in DMF (15 mL) was added triethylamine (0.43 mL, 3.11 mmol) and (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (0.26 g, 1.14 mmol) at room temperature. The reaction was stirred at 70° C. for 2 hours. The reaction was cooled to room temperature and treated with N,N′-diisopropylcarbodiimide (0.48 mL, 3.11 mmol). The reaction was then heated to 70° C. for 2 hours. The reaction was cooled to ambient temperature and concentrated. The crude product was purified by column chromatography (85% chloroform, 14% methanol, 1% ammonium hydroxide) to afford (R)—N-(6-fluoro-1H-indazol-3-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.22 g, 0.66 mmol, 64% yield) as a white powder. 1H NMR (500 MHz, DMSO-D6) δ ppm 12.16 (s, 1 H), 8.00 (s, 1 H), 7.59-7.67 (m, 1H), 7.09 (dd, J=9.77, 2.14 Hz, 1 H), 6.81-6.88 (m, 1 H), 3.81 (d, J=9.16 Hz, 1 H), 3.56 (d, J=8.85 Hz, 1 H), 3.00 (s, 2 H), 2.78 (s, 2 H), 2.67 (t, J=7.32 Hz, 2 H), 2.01 (d, J=2.44 Hz, 1 H), 1.92 (s, 1 H), 1.59 (d, J=5.80 Hz, 2 H), 1.46 (s, 1 H). MS (LC/MS) R.T.=1.44; [M+H]+=316.16.

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