Acetic Acid → HCID 67981004, compound

Participants

Reaction Steps

To a vial containing 4-((R)-3-morpholin-4-yl-1-phenylsulfanyl-methyl-propylamino)-N-(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-trifluoromethanesulfonyl-benzenesulfonamide (60 mg, 0.089 mmol) and 2-methyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (47.3 mg, 0.222 mmol) was added methanol (3 mL) under nitrogen. The reaction mixture was stirred in an ice bath for 10 minutes and then acetic acid (6.104, 0.107 mmol) was added. After stirring in the ice bath for an additional 15 minutes, sodium cyanoborohydride (44.6 mg, 0.710 mmol) was then added, and the reaction was stirred at ambient temperature for 15 hours. The reaction mixture was concentrated, filtered, and purified via flash chromatography on silica gel (10-50% 7N NH3 in methanol in CH2Cl2) to afford 2-methyl-4-{3-[4-((R)-3-morpholin-4-yl-1-phenylsulfanylmethyl-propylamino)-3-trifluoromethanesulfonyl-benzenesulfonylamino]-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl}-piperidine-1-carboxylic acid tert-butyl ester (42 mg, 53% yield). MS [m/z; (M+1)+]: 873.8

Provenance & Evidence