C(=O)([O-])[O-].Cl.[NH:6]([C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[NH2:7].C(O[CH:18]=[C:19]([C:22]#[N:23])[C:20]#[N:21])C>C(Cl)Cl.CO>[NH2:23][C:22]1[N:6]([C:8]2[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=2)[N:7]=[CH:18][C:19]=1[C:20]#[N:21]MP-carbonate (2.64 mmol/g) (2.6 g, 6.80 mmol) was added to 3-hydrazinyl-2-methylpyridine hydrochloride (Intermediate V2) (362 mg, 2.27 mmol) in DCM (10 mL). The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was filtered and evaporated. 2-(Ethoxymethylene)malononitrile (277 mg, 2.27 mmol) was added to suspension of the above solid in MeOH (6 mL) under nitrogen cooled to −5° C. The reaction mixture was stirred at 0° C. for 30 mins and then allowed to warm to room temperature and heated at reflux under nitrogen for 2 hours. The reaction mixture was allowed to cool and evaporated to dryness to afford the product (210 mg, 46.5%) which was used without further purification. 1H NMR (400 MHz, DMSO) δ 2.23 (3H, s), 6.65 (2H, s), 7.39-7.43 (1H, m), 7.74 (1H d), 7.79 (1H, s), 8.58-8.60 (1H, m), m/z (ESI+) (M+H)+=200; HPLC tR=1.21 min.
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