7-fluoro-1-((3aS,4S,6aR)-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine → 7-fluoro-1-((3aS,4S,6aR)-5-fluoro-2,2-dimethyltetrahydro-3aH-cyclopenta [d][1,3]dioxol-4-yl)-1H-imidazo [4,5-c]pyridin-4-amine

Participants

Reaction Steps

7-fluoro-1-((3aS,4S,6aR)-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta [d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine (5-9) (70 mg, 0.23 mmol, 1 equiv) was dissolved in MeOH (5 mL), the system was placed under nitrogen and 10% Pd/C (25 mg, 0.23 mmol, 1 equiv) was carefully added. The resulting mixture was stirred under a H2 atmosphere (1 atm) until disappearance of the starting material. Hydrogen was removed followed by filtration through a celite plug and washing of the solids with MeOH (4×20 mL). The filtrate was concentrated and the residue was purified via reverse phase chromatography (0-50% CH3CN in water with 0.1% TFA modifier) to afford 7-fluoro-1-((3aS,4S,6aR)-5-fluoro-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine (5-12) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.78 (d, J=3.5 Hz, 1H); 7.73 (s, 1H); 5.20-5.38 (m, 1H); 5.07 (s, 1H); 4.92 (m, 1H); 4.82 (s, 1H); 2.72-2.78 (m, 1H); 2.26-2.37 (m, 1H); 1.61 (s, 3H); 1.32 (s, 3H). LRMS m/z (M+H) 311.0 found, 311.1 required.

Provenance & Evidence