CO[C:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=1)=[C:4]([C:7]#[N:8])[C:5]#[N:6].Cl.[CH:18]([NH:21][NH2:22])([CH3:20])[CH3:19].C(N(CC)CC)C>C(O)C>[NH2:6][C:5]1[N:21]([CH:18]([CH3:20])[CH3:19])[N:22]=[C:3]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=2)[C:4]=1[C:7]#[N:8]Compound 33 (3.124 g, 11.3 mmol), isopropylhydrazine hydrochloride (1.27 g, 11.5 mmol) (purchased from Ryan Scientific) and triethylamine (6.40 mL, 46.0 mmol) were allowed to react in ethanol (75 mL) at room temperature for 1 hr. After concentrating the reaction mixture, it was purified by silica chromatography using a chloroform/methanol solvent system (methanol gradient increased with time from 0-10%). The relevant fractions were concentrated in vacuo to yield a yellow powder (3.15 g, 87% yield): 1H NMR (400 MHz, DMSO) δ 7.41 (m, 2H), 7.26 (td, J=7.7, 1.2, 1H), 7.21 (dt, J=7.7, 1.3, 1H), 6.50 (s, 2H), 4.38 (hept, J=6.5, 1H), 3.81 (s, 2H), 1.27 (d, J=6.5, 6H); 13C NMR (100 MHz, DMSO) δ 151.01, 150.15, 141.24, 131.05, 130.53, 129.16, 127.45, 121.55, 115.16, 71.77, 47.24, 32.88, 21.35; [M+H]+ calculated for C14H15BrN4 319.0, 321.0 found 318.9: 321.0.
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