Hydrochloric Acid → HCID 178509860, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-Cyano-5-{5-[4-(di-tert-butoxy-phosphoryloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine-2-carbonyl}-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (100 mg, 0.132 mmol) (Step 1) in anhydrous CH2Cl2 (5 mL) at 0° C. was added 4M HCl in Dioxane (0.331 mL, 1.32 mmol, 10 eq) and the solution warmed to 23° C. and stirred for 16 hr. The resulting suspension was concentrated under reduced pressure to afford Phosphoric-acid-mono-(1-{2-[4-cyano-3-(1H-pyrrolo[2,3-c]pyridin-4-yl)-benzoyl]-3H-imidazo-[4,5-b]pyridin-5-yl}-piperidin-4-yl)ester as a red-orange solid (75 mg, 0.122 mmol, 92%). HRMS m/z 544.1523 (M+H)+. 1H NMR (400 MHz, MeOD) δ: 9.24 (1H, s), 8.90 (s, 1H), 8.81 (d, J=8 Hz, 1H), 8.58 (s, 1H), 8.34 (d, J=3 Hz, 1H), 8.23 (d, J=8 Hz, 1H), 8.11 (d, J=9 Hz, 1H), 7.29 (d, J=9.5 Hz, 1H), 6.98 (d, J=2.5 Hz, 1H), 4.63 (m, 1H), 3.98 (m, 2H), 3.77 (m, 2H), 2.08 (m, 2H), 1.94 (m, 2H).

Provenance & Evidence