HCID 67430729, compound → HCID 67432108, compound

Participants

Reaction Steps

To a solution of the product of Step 1 (200 mg, 0.307 mmol) in ethyl acetate (1.5 mL) was added 10% Pd/C (65 mg, 0.061 mmol), and the vessel headspace was evacuated and purged with H2. The mixture was stirred under an atmosphere of H2 (balloon) for 3 hours, at which point LCMS analysis indicated incomplete reaction. The headspace was evacuated and purged with N2, then 100 mg additional catalyst was added and the headspace evacuated again and purged with H2. The catalyst was deactivated by adding dichloromethane, then the mixture was filtered through a pre-packed Celite cartridge (ethyl acetate rinse) and concentrated in vacuo. Purification by chromatography on silica gel (80:20 to 0:100, hexanes:ethyl acetate) provided 112 mg (0.180 mmol, 59%) of tert-butyl {3-amino-5-[2-(1-{[tert-butyl(dimethyl)silyl]oxy}cyclobutyl)-1,3-thiazol-5-yl]phenyl}[4-(trifluoromethyl)pyrimidin-2-yl]carbamate as a colorless oil.

Provenance & Evidence