C([N:3]([CH2:6]C)CC)C.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13](C(O)=O)=[C:12]2[NH:22][C@H:23]1[CH2:26][C@@H:25]([O:27][CH3:28])[CH2:24]1.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:30]C1C=CC=CC=1.O>CN(C=O)C>[Br:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[NH:3][C:6](=[O:30])[N:22]([C@H:23]4[CH2:24][C@@H:25]([O:27][CH3:28])[CH2:26]4)[C:12]=3[C:11]=2[CH:10]=1Triethylamine (39.3 mL, 281.89 mmol) was added to 6-bromo-4-[(cis-3-methoxycyclobutyl)amino]quinoline-3-carboxylic acid (33 g, 93.96 mmol) in DMF (200 mL) at r.t. After stirring for 30 minutes diphenyl phosphorazidate (28.4 g, 103.36 mmol) was added and the resulting mixture stirred at 60° C. for 2 h. The reaction mixture was poured into water (500 mL), the precipitate collected by filtration, washed with water (200 mL) and dried under vacuum to afford the desired material (32.0 g, 98%) as a yellow solid, which was used without further purification. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 2.75-2.82 (2H, m), 2.9-3.05 (2H, m), 3.22 (3H, s), 3.80-3.90 (1H, m), 4.85-4.99 (1H, m), 7.71 (1H, dd), 7.94 (1H, d), 8.48 (1H, d), 8.69 (1H, s), 10.42 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=348, 350.
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