I[C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7](O)=[O:8].[CH2:11]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(=O)([O-])[O-].[Na+].[Na+].CS(C)=O.[Cu]>[CH2:11]([C:18]1[CH:19]=[CH:20][C:21]2[NH:22][C:2]3[CH:3]=[N:4][N:5]([CH3:10])[C:6]=3[C:7](=[O:8])[C:23]=2[CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 8.0 g, 31.74 mmol), 4-benzylaniline (21.03 g, 114.76 mmol) and copper powder (3.2 g) in a mixture of 5% aqueous sodium carbonate (160 ml) and dimethylsulfoxide (80 ml) was stirred for 17 h at 100° C. After cooling to room temperature, the mixture was filtered through a pad of Celite, which was washed with water, 2N aqueous sodium hydroxide and diethyl ether. The separated water layer was washed with diethyl ether (100 ml×2). The water layer was acidified with concentrated hydrochloric acid and the formed solid was collected by filtration, dried, to give 4.86 g (50%) of the pure title compound as a pale brown solid.
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