Sodium Methoxide → 3-Amino-5-chloro-6-isopropoxy-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

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Reaction Steps

To a solution of N-cyclopropyl-2-mercapto-acetamide (0.498 g, 3.80 mmol) in MeOH (5 ml) is added sodium methoxide solution (25% wt. in MeOH)(0.652 ml, 2.85 mmol). The resulting solution is stirred at room temperature for 30 minutes, then treated with a 1:1 mixture of 2,5-dichloro-6-isopropoxy-4-methyl-nicotinonitrile and 5,6-dichloro-2-isopropoxy-4-methyl-nicotinonitrile (0.400 g, 1.63 mmol). The reaction vessel is sealed, heated at 100° C. for 2.5 hours, and cooled to room temperature. The reaction mixture is poured over water (60 ml), then extracted with EtOAc (2×40 ml). The combined organic layers are washed with brine (50 ml), dried (anhydrous magnesium sulfate), filtered, and concentrated to give a yellow-brown solid. Flash chromatography (1.5:1 hexane:EtOAc) affords the title compound as a tan solid (20 mg). Mass (m/z): 340.1 (M++1).

Provenance & Evidence