Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.CCOC(C)=O.CCCCCC.CCOC(C)=O>O1CCOCC1>[O:12]1[CH2:13][CH2:14][N:9]([C:2]2[S:3][CH:4]=[C:5]([CH:7]=[O:8])[N:6]=2)[CH2:10][CH2:11]1
To a slurry of 2-bromothiazole-4-carbaldehyde (1.0 g, 5.21 mmol) in p-dioxane (5 mL) was added morpholine (1.36 g, 15.61 mmol) over 1 min. The mixture was heated to 100° C. for 1 h (monitored by TLC, EtOAc/hexane 1:1) and cooled to room temperature. EtOAc (20 mL) was added and the solid residue filtered off and washed with EtOAc (30 mL). The combined organic layer was washed with brine (30 mL) and concentrated. The residue was purified by silica gel flash column chromatography using 20 to 75% EtOAc in hexane to afford the title compound as a light tan solid (780 mg, 75%): 1H NMR (400 MHz, CDCl3) δ 9.70 (s, 1H), 7.49 (s, 1H), 3.82 (t, 41-1, J=4.8 Hz), 3.56 (t, 4H, J=4.8 Hz). MS (ES) m/z 199.1 (M+H+).
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