[NH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:5][C:4](=[O:11])[CH:3]=1.C(NN)(C)(C)C.C(CC(OCC)=O)#N.[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH:30]=O.[C:36]1(=O)[CH2:40][CH2:39][C:38](=[O:41])[CH2:37]1>C(O)C>[Br:26][C:27]1[CH:28]=[C:29]([CH:30]2[C:3]3[C:4](=[O:11])[NH:5][N:6]([C:7]([CH3:8])([CH3:10])[CH3:9])[C:2]=3[NH:1][C:36]3[CH2:40][CH2:39][C:38](=[O:41])[C:37]2=3)[CH:32]=[CH:33][C:34]=1[F:35]5-Amino-1-tert-butyl-1,2-dihydropyrazol-3-one (0.23 g, 1.5 mmol), prepared by the method of (A. Weisberger and A. Porter, J. Amer. Chem. Soc, (1944) 66, 1849) from tert-butylhydrazine and ethyl cyanoacetate, 3-bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), and 1,3-cyclopentanedione (0.147 g, 1.5 mmol) in ethyl alcohol (3 mL) were heated at 80° C. for 2 days in a sealed tube. The solvent was evaporated under reduced pressure and the residue was chromatograhed on silica gel eluting with 10% ethanol/methylene chloride to provide 0.12 g of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 1.51 (s, 9H), 2.28 (m, 2H), 2.71 (m, 2H), 4.69 (s, 1H), 7.12 (m, 1H), 7.21 (t, 1H), 7.39 (dd, 1H), 9.43 (bs, 1H), 9.57 (s, 1H); MS (ESI−) m/z 420 (M−H)−; Anal. calcd for C19H19N3BrFO2: C, 54.17;H, 4.79; N, 9.97. Found: C, 54.17;H, 4.81; N, 9.85.
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