C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=2)[C:21]=1[NH2:22])=[O:16])[CH3:13].[CH:30]([S:33](Cl)(=[O:35])=[O:34])([CH3:32])[CH3:31].Cl>ClCCl>[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([C:23]2[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=2)[C:21]=1[NH:22][S:33]([CH:30]([CH3:32])[CH3:31])(=[O:35])=[O:34])=[O:16])[CH3:13]Add DBU (5.14 mL, 33.69 mmol) to a solution of 5-amino-1-(4-bromo-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.612 g, 8.42 mmol) in dichloromethane (25 mL) at 0° C. Stir for 15 min. at 0° C. and then add isopropylsulfonyl chloride (1.94 mL, 16.84 mmol). Immerse the mixture into a pre-heated oil bath (50° C.). After stirring for 5 min., add additional isopropylsulfonyl chloride (0.97 mL, 8.42 mmol). Stir overnight at 50° C. Add 1.0M HCl (aq) until pH 5, wash with water (2×50 mL), dry over sodium sulfate, filter, and concentrate. Adsorb the compound onto silica gel, and subject to silica gel flash column chromatography (15-30% EtOAc/n-hexane) to yield 1-(4-Bromo-phenyl)5-(propane-2-sulfonylamino)-1H-pyrazole-4-carboxylic acid ethyl ester (2.55 g, 73%).
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