Hydrochloric Acid → 4-(5-Nitro-benzooxazol-2-YL)-1,4-diaza-bicyclo[3.2.2]nonane

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Reaction Steps

The title compound was prepared from 2-methylsulfanyl-5-nitro-benzooxazole (prepared from 2-amino-4-nitrophenol by the methods described in Example 5 and Example 7) by the procedure described in Example 9 in 36% yield: 1H NMR (CDCl3, 400 MHz) δ 7.84 (d, 1H, J=2.1 Hz), 7.97 (dd, 1H, J=8.7, 2.1 Hz), 7.28 (d, 1H, J=8.7 Hz), 4.56-4.55 (m, 1H), 3 97 (t, 2H, J=5.8 Hz), 3.23-3.16 (m, 4H), 3.08-3.01 (m, 2H), 2.23-2.15 (m, 2H), 1.94-1.85 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 163.1, 152.8, 145.2, 144.3, 117.2, 111.7, 108.5, 56.4, 50.5, 45.9, 43.8, 26.3; MS (Cl) m/z 289.2 (M+1); HPLC retention time=3.11 min. The hydrochloride salt was prepared by diluting in ethyl acetate and adding a 2.5 N HCl solution in ethyl acetate: mp=240.2° C.

Provenance & Evidence