Diisopropylethylamine → 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

Participants

Reaction Steps

To a mixture of 3-{[(benzyloxy)carbonyl]amino}-7-(4-methyl-3-oxopiperazin-1-yl)quinoline-2-carboxylic acid (12.2 mg, 0.028 mmol), tert-butyl [(3R,4S,5S)-1-(3-aminopyridin-4-yl)-5-methyl-4-(1H-1,2,3-triazol-1-yl)piperidin-3-yl]carbamate (10.0 mg, 0.027 mmol), HATU (33 mg, 0.087 mmol), in DMF (0.29 mL), DIPEA (0.018 mL, 0.10 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with MeOH and H2O, filtered and 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 60 mL/min.) to give the sub-title compound as a bright yellow powder (12 mg, 57%). LCMS calc. for C41H48N11O6 (M+H)+: m/z=790.4. Found: 790.3.

Provenance & Evidence