Cl[C:2]1[C:7]([C:8]([NH2:10])=[S:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:11][CH2:12]O.Br[CH:15](CC)[C:16](=O)[C:17]([O-:19])=[O:18].CO.C(Cl)[Cl:26]>CCOC(C)=O>[Cl:26][C:4]1[N:5]=[CH:6][C:7]([C:8]2[S:9][CH:15]=[C:16]([C:17]([O:19][CH2:11][CH3:12])=[O:18])[N:10]=2)=[CH:2][CH:3]=1To a mixture of the 4-chloro-thionicotinamide (5.5 g, 31.9 mmol) and EtOH (300 mL) was added bromo-ethyl-pyruvate (4.4 mL, 35.1 mmol). The mixture was heated at reflux for 15 h, cooled and concentrated in vacuo to afford a yellow solid/orange oil. The oil was diluted with EtOAc and filtered off yellow solid. The filtrate was filtered through Celite® and concentrated in vacuo to give a dark yellow oil. The oil was diluted with 2% MeOH/CH2Cl2 and filtered through a pad of silica gel (150 mL). Elution with 2% MeOH/CH2Cl2 (500 mL), followed by concentration in vacuo afforded the title compound as a yellow crystalline solid. MS m/z: 269.1 (M+H).
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