Hydrochloric Acid → N-(4-{4-amino-7-[(1E)-3-(3-aminopiperidin-1-yl)prop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

Participants

Reaction Steps

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 piperidin-3-ylcarbamate (124 mg, 0.621 mmol), were reacted according to General Procedure B. The crude product (137 mg, 0.206 mmol) was dissolved in methanol (1 mL) and treated with 6.0 M hydrochloric acid in 1,4 dioxane (0.514 mL, 2.06 mmol) and heated to 55 degrees Celsius for 20 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 HPLC preparation to furnish the title compound as an ivory powder (23.0 mg, 0.0406 mmol): LCMS (Conditions a): MH−=565 RT=3.35 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.45 (1 H), 7.91 (2 H), 7.65 (1 H), 7.28 (3 H), 7.10 (3 H), 7.01 (1 H), 6.64 (1 H), 6.15 (1 H), 5.59 (1 H), 3.71 (3 H), 3.85 (3 H), 3.52 (1 H), 3.14 (2 H), 2.89 (1 H), 2.78 (1 H), 2.62 (1 H), 2.16 (1 H), 2.03 (1 H), 1.66 (1 H), 1.42 (1 H), 1.15 (1 H).

Provenance & Evidence