[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl.O[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH:21]=1)C(O)=O.COC(=O)C1C=C(O)[CH:28]=[N:27]C=1.C([N:35](CC)CC)C>ClCCl.CN(C)C=O>[N:15]1[CH:14]=[CH:13][CH:21]=[CH:17][C:16]=1[C:28]1[N:27]=[C:7]([C:6]2[CH:5]=[N:4][CH:3]=[C:2]([OH:1])[CH:10]=2)[O:8][N:35]=1
In a similar fashion, 5-hydroxynicotinoyl chloride was prepared from 5-hydroxynicotinic acid hydrochloride, which was obtained form the hydrolysis of 5-hydroxynicotinic acid methyl ester (1.53 g, 10 mmol). Treatment of the acid chloride with pyrid-2-ylamidoxime (1.37 g, 10 mmol) and triethylamine (4.04g, 40 mmol) in dichloromethane (10 mL), followed by heating in dimethylformamide (20 mL) at 120° C. for 2 hours afforded 497 mg (21%) 3-(2-pyridyl)-5-(5-hydroxy-pyrid-3-yl)-1,2,4-oxadiazole.
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