P(Cl)(Cl)(OC)=O.[CH3:7][O:8][C:9]1[N:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([NH2:19])=O)[CH:12]=[CH:11][C:10]=1[N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1.C1CCN2C(=NCCC2)CC1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH3:7][O:8][C:9]1[N:14]=[C:13](/[CH:15]=[CH:16]/[C:17]#[N:19])[CH:12]=[CH:11][C:10]=1[N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1Methyl dichlorophosphate (33 ml) was added dropwise to a suspension of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide (42.96 g) and 1,8-diazabicyclo[5,4,0]-7-undecene (112 ml) in methylene chloride (400 ml) under ice-cooling over 20 minutes. The reaction solution was stirred at the same temperature for 10 minutes and at room temperature for further 35 minutes. Then, a saturated sodium bicarbonate solution (200 ml) was added to the reaction solution, and the reaction solution was stirred at room temperature for 10 minutes. Water was added to the reaction solution. Then, the reaction solution was filtered and the organic layer in the filtrate was separated. The aqueous layer was reextracted with methylene chloride (twice). The combined organic layers were dried over anhydrous magnesium sulfate and purified by short silica gel column chromatography (carrier: Chromatorex NH; elution solvent: methylene chloride). The eluted fraction was concentrated. The resulting residue was triturated with ethyl acetate and tert-butyl methyl ether and dried under reduced pressure overnight to obtain 34.28 g of the title compound.
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