Cl.O1CCOCC1.[C:8]([C:10]1[C:11]([O-])=[N:12][CH:13]=[C:14]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]2)[CH:15]=1)#[N:9].[Na+].P(Cl)(Cl)([Cl:30])=O.[OH-].[Na+]>C(#N)C.O.C(O)(C)C>[Cl:30][C:11]1[N:12]=[CH:13][C:14]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]2)=[CH:15][C:10]=1[C:8]#[N:9]A 4.0 M solution of hydrogen chloride in dioxane (1.33 ml, 5.31 mmol) was added to a stirred suspension of sodium 3-cyano-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-olate (1.5 g, 5.31 mmol; see Method 21) in acetonitrile (15 ml). The mixture was heated to 40° C. and phosphorous oxychloride (2.48 ml, 26.6 mmol) added then the mixture was heated at 80° C. for 18 hours. After cooling to room temperature, isopropyl alcohol (8 ml) was added and the mixture stirred for 10 minutes. The mixture was diluted with water (50 ml) and basified with a solution of sodium hydroxide (1M) to pH 8. The product was extracted with dichloromethane (2×100 ml), the extracts dried over magnesium sulfate, filtered and concentrated to yield the title compound as a brown oil (1.2 g, 81%).
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