C(N(CC)CC)C.Cl.Cl.[NH2:10][C:11]([CH3:33])([CH3:32])[CH2:12][N:13]1[C:25]2[C:24]3[N:23]=[CH:22][C:21]([Br:26])=[CH:20][C:19]=3[N:18]=[C:17]([NH2:27])[C:16]=2[N:15]=[C:14]1[CH2:28][O:29][CH2:30][CH3:31].[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[NH2:27][C:17]1[C:16]2[N:15]=[C:14]([CH2:28][O:29][CH2:30][CH3:31])[N:13]([CH2:12][C:11]([NH:10][S:35]([CH3:34])(=[O:37])=[O:36])([CH3:32])[CH3:33])[C:25]=2[C:24]2[N:23]=[CH:22][C:21]([Br:26])=[CH:20][C:19]=2[N:18]=1Triethylamine (13.02 g, 128.7 mmol) was added to a suspension of 1-(2-amino-2-methylpropyl)-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine dihydrochloride (6.00 g, 12.9 mmol) in dichloromethane (500 mL), and the reaction was cooled to 4° C. A solution of methanesulfonyl chloride (1.62 g, 14.2 mmol) in dichloromethane (10 mL) was then added dropwise. The reaction mixture was allowed to warm to room temperature, stirred for 24 hours, diluted with dichloromethane (200 mL), washed sequentially with water (200 mL), 4% aqueous sodium carbonate (2×200 mL), water (200 mL), and brine (200 mL), and concentrated under reduced pressure. The crude product was purified by automated flash chromatography (FLASH 40+M silica cartridge, eluting with 0 to 25% CMA in chloroform) followed by recrystallization from acetonitrile to provide 5.21 g of N-{2-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-1,1-dimethylethyl}methanesulfonamide as a white solid, 211-212° C.
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