[C:1]([C:3]1[C:4]([I:13])=[C:5]([C:10](O)=[O:11])[S:6][C:7]=1[S:8][CH3:9])#[N:2].Cl.C[N:16](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>C(Cl)Cl.CO.O>[C:1]([C:3]1[C:4]([I:13])=[C:5]([C:10]([NH2:16])=[O:11])[S:6][C:7]=1[S:8][CH3:9])#[N:2]To a suspension of 4-cyano-3-iodo-5-(methylsulfanyl)thiophene-2-carboxylic acid (2.85 g, 7.93 mmol) in methylene chloride (30 mL), were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.28 g, 17.1 mmol) and 1-hydroxybenzotriazole (2.27 g, 16.8 mmol). The reaction mixture was stirred at room temperature for two hours and ammonium hydroxide (15.4 mL) was added and the biphasic mixture was stirred at room temperature for two hours. Water (100 mL), methanol (50 mL), methylene chloride (200 mL) was added. The organic layer was removed. The aqueous layer was extracted five times with a solution of 20% methanol in methylene chloride (100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to the title compound as dark red oil (1.47 g, 57%). LCMS: (FA) ES+ 325.
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