Benzyl [2-[({4-[(3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(4-methyl-3-oxopiperazin-1-yl)quinolin-3-yl]carbamate → Benzyl carbamate

Participants

Reaction Steps

A solution of benzyl [2-[({4-[(3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(4-methyl-3-oxopiperazin-1-yl)quinolin-3-yl]carbamate (12.0 mg, 0.015 mmol) in MeOH (1.0 mL) was hydrogenated in the presence of 10% palladium on carbon (6.0 mg) under a balloon of hydrogen for 1 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give a benzyl carbamate deprotected intermediate. The intermediate was treated with 4.0 M HCl in dioxane (0.15 mL, 0.6 mmol) at room temperature for 1 h. The solution was concentrated under reduced pressure and the resulting residue was diluted with MeOH and NH4OH, filtered. The filtrate was purified by preparative LCMS (XBridge™ C18 column, eluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.) to give the title compound as a yellow powder (5.1 mg, 60%). LCMS calc. for C28H34N11O2 (M+H)+: m/z=556.3. Found: 556.3.

Provenance & Evidence