Hydrochloric Acid → 3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(2,7-diazaspiro[4.4]nonan-2-yl)pyrazin-2-amine

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Reaction Steps

tert-Butyl 7-[5-[bis(tert-butoxycarbonyl)amino]-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-3,7-diazaspiro[4.4]nonane-3-carboxylate (50.9 mg, 0.07668 mmol) was treated with a solution of hydrogen chloride (192 μL, of 4 M, 0.77 mmol) in dioxane. The reaction mixture was stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in DMF and purified by reverse phase HPLC using (1-99% ACN/H2O (5 mM HCl)) to yield 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(2,7-diazaspiro[4.4]nonan-2-yl)pyrazin-2-amine. 1H NMR (400 MHz, DMSO-d6) δ 9.34 (s, 2H), 8.25-7.99 (m, 2H), 7.89 (s, 1H), 7.66 (d, J=6.6 Hz, 3H), 3.60-3.47 (m, 4H); 3.36-3:25 (m, 2H), 3.18 (tt, J=12.1, 6.0 Hz, 2H), 2.19-1.83 (m, J=17.8, 12.7, 5.9 Hz, 4H); LC/MS m/z 364.1 [M+H]+.

Provenance & Evidence