F[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CS(C)=O.CCN(C(C)C)C(C)C.[Cl-].[CH3:24][N:25]([CH3:32])[S:26]([CH2:29][CH2:30][NH3+:31])(=[O:28])=[O:27]>CCOC(C)=O>[C:8]([C:3]1[C:2]([NH:31][CH2:30][CH2:29][S:26]([N:25]([CH3:32])[CH3:24])(=[O:28])=[O:27])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:9]3-fluoro-2-cyanopyridine (Sakamoto et. al., Chem. Pharm. Bull. 1985, 33: 565-571) (1 g, 8.2 mmol) was placed in a high pressure tube equipped with a stir bar. DMSO (7 mL), Hunig's base (1.57 mL, 9.0 mmol) and 2-[(dimethylamino)sulfonyl]-ethanaminium chloride (1.7 g, 9.0 mmol) were added and the vessel was sealed and heated to 80° C. for 5.5 hours, then stirred at room temperature overnight. The reaction was treated with an additional 0.3 equivalent of Hunig's base and 0.2 equivlanet of the amine salt and heated for 3 hours, but the reaction progressed no further. The mixture was cooled, added to the top of a silica gel column (60 mm by 7 inches) packed in EtOAc and the column eluted with EtOAc. Careful cutting of fractions allowed isolation of the product after evaporation as a clear, colorless oil that solidified upon standing.
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