Diisopropylethylamine → tert-Butyl methyl [(3R,4S,5S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-bromoquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidine-3, 4-diyl]biscarbamate

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Reaction Steps

To a mixture of 3-{[(benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylic acid (360 mg, 0.897 mmol), tert-butyl methyl [(3R,4S,5S)-1-(3-aminopyridin-4-yl)-5-methylpiperidine-3,4-diyl]biscarbamate (303 mg, 0.799 mmol) and HATU (914.8 mg, 2.406 mmol) in DMF (5.0 mL), DIPEA (539 mg, 4.17 mmol) was added. The mixture was stirred at room temperature for 3 h. The volatile solvents were removed under reduced pressure, and the residue was purified by flash chromatography (40 g, 0-100% EtOAc in hexanes) to give the sub-title compound as a red viscous oil (1.120 g, 184%). The product was used in the next step without further purification. LCMS calc. for C36H41BrN7O7 (M+H)+: m/z=762.2. Found: 762.3.

Provenance & Evidence