Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:13][CH2:12][CH2:11][NH:10][CH2:9]1.C(N(CC)CC)C.Cl[C:22]1[N:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][CH:23]=1.C(OCC)(=O)C>CS(C)=O>[N+:29]([C:25]1[C:26]([NH2:28])=[N:27][C:22]([N:10]2[CH2:11][CH2:12][O:13][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=3)[CH2:9]2)=[CH:23][CH:24]=1)([O-:31])=[O:30]To a solution of 2-(pyridin-2-yl)morpholine hydrochloride (1000 mg, 4.22 mmol) and triethylamine (1.3 mL, 9.3 mmol) in dimethylsulfoxide (10 mL) was added 6-chloro-3-nitropyridin-2-amine (734 mg, 4.23 mmol). The reaction mixture was stirred at 100° C. for 18 h. The reaction mixture was cooled to room temperature. Ethyl acetate was added and the mixture was washed with water (20 mL). The aqueous layer was extracted with ethyl acetate (20 mL×2). The combined organics were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (40-100% ethyl acetate in heptanes) to afford the title compound (0.897 g, 70%). 1H NMR (400 MHz, CDCl3) δ 3.08 (s, 1H), 3.18-3.29 (m, 1H), 3.83 (s, 1H), 4.20 (s, 1H), 4.41 (d, 1H), 4.63 (dd, 1H), 4.67-4.80 (m, 1H), 6.18 (s, 1H), 7.23-7.26 (m, 1H), 7.54 (s, 1H), 7.75 (s, 1H), 8.22 (s, 1H), 8.60 (s, 1H).
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