[CH3:1][O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([OH:13])=O)[CH:6]=1)=[O:4].S(Cl)(Cl)=O.CC(C)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>O>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([N:22]=[N+:23]=[N-:24])=[O:13])[CH:6]=1)=[O:4]
1-Methyl-1H-pyrazole-3,5-dicarboxylic acid 5-methyl ester (641, 3.2 g, 17.0 mmol) was combined with thionyl chloride (5 mL). The reaction was heated to reflux for 40 minutes and then concentrated twice from toluene. The resulting solid was dried under reduced pressure overnight. The product was dissolved into acetone (20 mL) and sodium azide (3.5 g, 54.0 mmol) was added in water (10 mL) rapidly at once. The obtained solution was stirred for one minute and then poured into ice-water (50 mL). The precipitate was filtered and dried under reduced pressure. The final compound was used without further purification (642, 2.8 g, 77%).
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