HCID 117637152, compound → HCID 71522951, compound

Participants

Reaction Steps

To a suspension of Pd/C (25 mg, 0.235 mmol) in methanol (3 mL) under N2 was added N-[(1S)-1-{5-[(1R)-1-{[(2-chloroimidazo[1,2-a]pyrazin-6-yl)sulfonyl](3,3-dimethylbutyl)amino}-2-hydroxyethyl]thiophen-2-yl}-2,2,2-trifluoroethyl]-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (7.5 mg, 9.13 μmol). The resulting slurry was purged under vacuum and backfilled with H2 three times, after which the mixture was stirred for 16 hours at room temperature. Since LCMS showed only 50% conversion, the reaction mixture was transferred to a pressure flask and hydrogenated at 50 psi of H2 for 3 days, after which Pd/C (25 mg, 0.235 mmol) was added and the mixture was hydrogenated at 50 psi for 6 hours. The reaction mixture was filtered over a Celite pad, and the volatile components were evaporated under reduced pressure. The crude residue was purified by flash chromatography (Combiflash® Rf system; SiO2 4 grams Cat. No. 69-2203-304, solvent flow 18 mL/minute, elution gradient of 20-100% (EtOAc/hexanes). The fractions containing the desired product were pooled and evaporated under reduced pressure to afford the title material as a colorless oil. MS: m/z=787.2 ((MH+)).

Provenance & Evidence