[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[H-].[Na+].[CH3:9][S:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([C:24](F)=[O:25])=[CH:13][N:12]=1.Cl>CN(C=O)C>[NH2:2][C:1]1[N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15]2[N:16]=[C:11]([S:10][CH3:9])[N:12]=[CH:13][C:14]=2[C:24](=[O:25])[C:3]=1[C:4]([NH2:6])=[O:5]To a solution of 1.0 g (11.96 mmol) of cyanoacetamide in 17 mL of anhydrous DMF, cooled to 0-5°C., is added 0.96 g (23.93 mmol) of 60% NaH. After the addition, the mixture is stirred for 10 minutes at room temperature and then cooled again on an ice-water bath, and a solution of 3.0 g the acid fluoride (11.39 mmol) prepared in step 20.3 in 17 mL of anhydrous DMF is added. The reaction mixture is stirred at room temperature overnight. The reaction mixture is cooled on an ice-water bath, and 0.48 g (11.96 mmol) of 60% NaH is added. The reaction mixture is stirred for 5 hours at room temperature and then poured into ice-cold aqueous 0.5 N HCl solution. The precipitate formed is isolated by filtration, rinsed with water, drained by suction and then dried in an oven. 3.44 g of a yellow solid mainly composed of the expected product in non-cyclized form are obtained.
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