Acetic Acid → HCID 66673244, compound

Participants

Reaction Steps

Dissolve ((R)-1-{5-[2-(4-chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno [2,3-c]pyridin-6-yl]-pyridin-2-yl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (0.393 g, 0.750 mmol) in CHCl3 (5 mL) and treat with TFA (2 mL). Stir the mixture at RT for 30 min. Remove the excess reagent in vacuo. Dissolve the crude material in CH3OH (10 mL) and treat with HOAc (90.22 mL, 3.93 mmol), and (1-ethoxy-cyclopropoxy)trimethylsilane (0.47 mL, 2.36 mmol). Stir the mixture at RT for 10 min. Add NaBH3CN (90.36 g, 5.69 mmol) and reflux the reaction overnight. Dilute the mixture with EtOAc (50 mL) and 2.0 M NaOH (920 mL) and then stir at RT for 5 min. Filter and wash the mixture with EtOAc (30 mL). Separate the organic layer and dry with Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 5% CH3OH (2M NH3)/CHCl3 to give 0.35 g (93%) of 2-(4-chloro-phenyl)-6-[6-((R)-3-dicyclopropylamino-pyrrolidin-1-yl)-pyridin-3-yl]-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one.

Provenance & Evidence