[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:5][CH:6]=1.C(N(CC)CC)C.C(NC1C=CC(S([N:33]=[N+:34]=[N-])(=O)=O)=CC=1)(=O)C>C(#N)C>[N+:33](=[C:7]([C:4]1[S:5][CH:6]=[C:2]([CH3:1])[N:3]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N-:34]A solution of ethyl (4-methyl-1,3-thiazol-2-yl)acetate (ENAMINE, 300 mg, 1.619 mmol) in acetonitrile (ACN) (12 mL) was treated with triethylamine (FLUKA, 0.339 mL, 2.429 mmol) at 0° C. After 20 minutes 4-acetamidobenzenesulfonyl azide (ALDRICH, 389 mg, 1.619 mmol) was added and the mixture was allowed to reach room temperature overnight. Then, 4-acetamidobenzenesulfonyl azide (ALDRICH, 94 mg, 0.391 mmol) was added and continued stirring at room temperature for 2 h. Reaction mixture was concentrated and residue was triturated with a mixture 1:1 Et2O-hexane and filtered. Solid was washed several times with the same mixture. The filtrate was concentrated to give 310 mg of crude. It was purified on a 10 g silica cartridge and eluted manually with linear gradient 0-50% hexane-ethyl acetate to yield the title compound (200 mg, 0.947 mmol, 58.5% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 7.49 (d, 1H), 4.34 (q, 2H), 2.60 (s, 3H), 1.32 (t, 3H). [ES+MS] m/z 212 (MH+).
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