[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:47][O:48][C:49]1[N:54]=[C:53]([CH2:55]O)[CH:52]=[CH:51][CH:50]=1>ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][CH2:55][C:53]1[CH:52]=[CH:51][CH:50]=[C:49]([O:48][CH3:47])[N:54]=14-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-ol (25 mg, 0.093 mmol) and triphenylphosphine (32 mg, 0.12 mmol, 1.3 equiv) were dissolved in dichloromethane (0.5 mL). To the stirring mixture was added diethyl diazene-1,2-dicarboxylate (25 mg, 0.12 mmol, 1.3 equiv), followed by (6-methoxypyridin-2-yl)methanol (16 mg, 0.11 mmol, 1.2 equiv) and the mixture stirred at ambient temperature for 14 hours. The mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (5: 95 to 95:5; acetonitrile:water containing 0.1% trifluoroacetic acid), providing the title compound as a clear oil: 1H-NMR (400 MHz, d6-DMSO) δ 7.94 (1H, d, J=9.1 Hz), 7.76 (1H, t, J=7.7 Hz), 7.60 (1H, d, J=8.9 Hz), 7.21 (1H, d, J=7.9 Hz), 6.77 (1H, d, J=7.9 Hz), 5.32, (2H, s), 4.59 (2H, d, J=7.31 Hz), 3.84 (3H, s), 1.40-1.32 (1H, m), 0.56-0.53 (2H, m), 0.48-0.44 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 389.0617 [(M+H)+; calculated for C17H17BrN4O2: 389.0607].
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