[CH:1]([C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=1)=O.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CO>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:1][C:3]2[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=2)[CH2:15][CH2:14]1To a solution of 6-formyl-2-pyridinecarboxylic acid [Chemstep Product List] (0.25 g) in dichloromethane (6.8 ml) was added 1-methylpiperazine (0.481 ml) and acetic acid (0.083 ml). The mixture was stirred at room temperature for 15 min when sodium triacetoxyborohydride (0.459 g) was added and the mixture stirred overnight. The crude reaction mixture was diluted with dichloromethane (60 ml) and methanol was added until a clear solution was observed. The mixture was loaded onto an aminopropyl-SPE cartridge (5 g) pre-eluted with dichloromethane. The cartridge was eluted with dichloromethane and methanol and fractions containing product were combined and blown to dryness under a stream of nitrogen. The crude product was taken up in dichloromethane (2×25 ml) and washed with 2M sodium hydroxide solution (25 ml). The aqueous layer was acidified to pH7 using 5N hydrochloric acid and concentrated under vacuum to approximately 25 ml. The solution was loaded onto an Oasis cartridge (6 g) and eluted with water (one volume) and methanol. Fractions containing product were combined and dried to give the title compound (0.171 g).
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