Example 133
A suspension of N,N′-disuccinimidyl carbonate (85 mass %), o-methylhydroxylamine HCl (0.03198 g, 0.3753 mmol,), and DIPEA (0.06790 g, 0.5254 mmol,) in ACN (1 ml) was stirred at RT for 0.5 h. 6-(4-Methyl-3-quinolyl)spiro[4H-1,3-benzodioxine-2,4′-piperidine] (52 mg, 0.1501 mmol), and DIPEA (0.06790 g, 0.5254 mmol,) were added and stirred 0.5 h. The reaction was then partitioned between EtOAc and water, separated and the organic layer back extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. The product was purified by Gilson (5-45% ACN in water with 0.1% TFA). The pure fractions were concentrated, freebased, and dried at 50° C. overnight to give a solid. Analysis: LCMS m/z=420 (M+1); 1H NMR (400 MHz, DMSO-d6) δ: 9.82 (s, 1H), 8.72 (s, 1H), 8.19 (dd, J=8.4, 0.9 Hz, 1H), 8.04 (dd, J=8.5, 1.0 Hz, 1H), 7.77 (ddd, J=8.3, 6.9, 1.4 Hz, 1H), 7.72-7.64 (m, 1H), 7.29 (dd, J=8.3, 2.3 Hz, 1H), 7.22 (d, J=2.0 Hz, 1H), 7.01 (d, J=8.3 Hz, 1H), 4.95 (s, 2H), 3.55 (s, 3H), 3.49-3.34 (m, 4H), 2.63 (s, 3H), 1.92-1.78 (m, 4H).
