C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1.C(N(CC)CC)C.[CH3:26][C:27]1[O:31][C:30]([C:32](O)=[O:33])=[C:29]([O:35][CH:36]([CH3:38])[CH3:37])[CH:28]=1.C(C1NN=NN=1)(=O)N>C(#N)C>[CH3:26][C:27]1[O:31][C:30]([C:32]([NH:13][C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[O:33])=[C:29]([O:35][CH:36]([CH3:38])[CH3:37])[CH:28]=1Following the procedure described in Example 120, 0.60 g (3.7 mmol, 1.1 equiv) of 1,1'-carbonyl diimidazole, 0.33 g (3.9 mmol, 1.2 equiv) of 5-aminotetrazole and 0.80 g (7.9 mmol, 2.4 equiv) of triethylamine in refluxing (16 hours) acetonitrile (15 mL) are used to convert 0.61 g (3.3 mmol) of the carboxylic acid described above to 0.45 g of the carbamoyltetrazole as a tan solid. Recrystallization gave 0.35 g (1.26 g theo., 28% overall) of analytically pure 5-methyl-3-isopropoxy-N-1H-tetrazol-5-yl-2-furancarboxamide as a tan, crystalline solid; mp 240°-242° C. (dec).
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