N-(4-{4-Amino-7-[(1E)-3-oxoprop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (100 mg, 0.207 mmol) and tert-butyl pyrrolidin-3-ylcarbamate (115.7 mg, 0.621 mmol) were reacted according to General Procedure B. The crude product (135 mg, 0.207 mmol) was dissolved in methanol (1 mL) and treated with 6.0 M hydrochloric acid in 1,4 dioxane (0.518 mL, 2.07 mmol) and heated to 55 degrees Celsius for 4 hours. The mixture was cooled to room temperature then 1M sodium carbonate solution (5 mL) was added and product was extracted with ethyl acetate (3×10 mL). The organic layer was separated, dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The product was purified via flash chromatography to furnish the title compound as an ivory powder (22.5 mg, 0.0408 mmol): LCMS (Conditions a): MH−=551 RT=3.62 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.51 (1 H), 7.97 (2 H), 7.72 (1 H), 7.63 (2 H), 7.36 (2 H), 7.21 (1 H), 7.15 (1 H), 7.07 (1 H), 6.70 (1 H), 6.26 (1 H), 5.65 (1 H), 4.04 (3 H), 3.91 (3 H), 3.51 (1 H), 3.29 (2 H), 2.71 (2 H), 2.45 (2 H), 2.10 (1 H), 1.53 (1 H).
