[CH3:1]I.[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[NH:14][C:15](=[O:23])[N:16]([C@H:17]4[CH2:20][C@@H:19]([O:21][CH3:22])[CH2:18]4)[C:7]=3[C:6]=2[CH:5]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[N:14]([CH3:1])[C:15](=[O:23])[N:16]([C@H:17]4[CH2:18][C@@H:19]([O:21][CH3:22])[CH2:20]4)[C:7]=3[C:6]=2[CH:5]=1Methyl iodide (11.49 mL, 183.81 mmol) was added to a mixture of 8-bromo-1-(cis-3-methoxycyclobutyl)-3H-imidazo[4,5-c]quinolin-2-one (32 g, 91.90 mmol), sodium hydroxide (5.51 g, 137.85 mmol) and tetrabutylammonium bromide (2.94 g, 9.19 mmol) in DCM (400 mL) and water (300 mL) and the resulting mixture stirred at r.t. for 2 h. The DCM was removed in vacuo and the precipitate collected by filtration, washed with water (200 mL) and dried under vacuum to afford the desired material (25.00 g, 75%) as a pale yellow solid. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 2.72-2.86 (2H, m), 2.9-3.08 (2H, m), 3.22 (3H, s), 3.49 (3H, s), 3.85-3.89 (1H, m), 4.88-5.06 (1H, m), 7.74 (1H, dd), 7.98 (1H, d), 8.50 (1H, d), 8.92 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=362, 364.
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