[Cl:1][C:2]1[CH:24]=[N:23][C:5]2[N:6](COCC[Si](C)(C)C)[C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=3[C:4]=2[C:3]=1[N:25]1[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26]1.Br.[OH-].[Na+].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:24]=[N:23][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=3[C:4]=2[C:3]=1[N:25]1[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26]1(S)-3-Chloro-4-(3-hydroxypyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (100 mg, 0.2 mmol) was dissolved in 1,4-dioxane (0.3 mL) and then treated with 48% HBr(aq) (0.3 mL) and heated at 55° C. for 20 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 (2 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 pale off-white solid (40 mg, 60% over two steps). 1H NMR (400 MHz, d6-DMSO) δ 8.95 (s, 1H), 8.56 (s, 1H), 8.45 (s, 1H), 5.27 (s, 1H), 4.54 (s, 1H), 3.88 (m, 1H), 3.78 (dd, J=10.5, 4.6, 1H), 3.66 (td, J=9.0, 4.5, 1H), 3.50 (d, J=10.3, 1H), 2.34-2.19 (m, 1H), 2.06-1.95 (m, 1H), NH signals not observed. LCMS (Method D): RT=8.57 min, M+H+=314.0.
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