[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([CH2:12][O:13][C:14]2[C:22]3[C:21]4[CH:23]=[C:24]([C:27]#[N:28])[N:25]=[CH:26][C:20]=4[N:19](COCC[Si](C)(C)C)[C:18]=3[N:17]=[CH:16][CH:15]=2)([CH3:11])[CH2:7][CH2:6]1.Br.[OH-].[Na+].Cl>O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([CH2:12][O:13][C:14]2[C:22]3[C:21]4[CH:23]=[C:24]([C:27]#[N:28])[N:25]=[CH:26][C:20]=4[NH:19][C:18]=3[N:17]=[CH:16][CH:15]=2)([CH3:11])[CH2:7][CH2:6]14-((1-(2-methoxyethyl)-4-methylpiperidin-4-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (36 mg, 0.07 mmol) was dissolved in 1,4-dioxane (0.3 mL) and then treated with 48% HBr(aq) (0.3 mL) and heated at 75° C. for 15 minutes. The cooled reaction mixture was then basified to pH ˜12 by dropwise addition of 6N sodium hydroxide and then immediately acidified to pH ˜8-9 by dropwise addition of concentrated hydrochloric acid, producing a cloudy precipitate. The solid was collected by centrifugation, dissolved in dimethylsulfoxide (1 mL), and purified by preparative HPLC [5-85% methanol in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min] to afford the title compound as a white solid (7 mg, 25%). 1H NMR (500 MHz, d6-DMSO) δ 8.99 (s, 1H), 8.55 (d, J=5.7, 1H), 8.35 (s, 1H), 8.31 (s, 1H), 7.08 (d, J=5.8, 1H), 4.13 (s, 2H), 3.44 (t, J=6.4, 2H), 3.24 (s, 3H), 2.66-2.58 (m, 2H), 2.52 (t, J=6.4, 2H), 2.39 (m, 2H), 1.74 (m, 2H), 1.53 (m, 2H), 1.18 (s, 3H). LCMS (Method G): RT=3.92 min, M+H+=380.0.
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