[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([OH:13])=O.CC[N:16]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([NH2:16])=[O:13]A solution of the compound (10.29 g, 41.64 mmol) obtained in step 3, WSC (9.58 g, 49.97 mmol), HOBt (6.75 g, 49.97 mmol), TEA (6.97 ml, 49.97 mmol) and ammonium chloride (2.67 g, 49.97 mmol) in DMF (100 mL) was stirred at room temperature for 14 hr. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic layer was washed with water, aqueous sodium hydrogen carbonate solution and saturated brine and dried, and the solvent was evaporated under reduced pressure to give 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxamide (6.18 g, 25.1 mmol, 60%) as a white powder.
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