[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(N[C:12]1[CH:13]=[CH:14][C:15](O)=[C:16]([CH:20]=1)[C:17]([NH2:19])=[O:18])(=O)C.N1CCOCC1>CO.C(OCC)(=O)C>[NH:1]1[CH2:6][CH2:5][C:4]2([NH:19][C:17](=[O:18])[C:16]3[CH:20]=[CH:12][CH:13]=[CH:14][C:15]=3[O:7]2)[CH2:3][CH2:2]1A mixture of 24 mg (0.077 mmol) of N-[4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone, 15 mg (0.077 mmol) of 5-acetamido-2-hydroxybenzamide, and 0.020 mL of morpholine in 3 mL of methanol is refluxed for 48 hr. The reaction mixture is diluted with ethyl acetate, and washed with water, brine, and dried over Na2SO4. After solvent removal by rotoevaporation, the crude product is purified by preparative TLC to give 11 mg (0.022 mmol, 30% yield) of 6-acetamido-1′-[4,8-dimethoxyquinoline-2-yl)carbonyl]spiro[2H-1,3-benzoxazin-2,4′-piperidin]-4-(3H)-one (Compound 9): 1H NMR (DMSO-d6): δ 2.02 (s, 3H), 3.95 (s, 3H), 4.06 (s, 3H), 7.03 (d, 1H), 8.19 (s, 1H), 7.24 (d of d, 1H), 7.52 (d of d, 1H), 7.67 (m, 2H), 8.02 (d, 1H), 8.82, (s, 1H) and 9.98 ppm (s, 1H). MS m/z: 491.1 (M+H)+, 513.2 (M+Na)+.
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