Triethylamine → 7-Chloro-3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

Participants

Reaction Steps

6-Morpholinonicotinic acid (32.6 mg, 0.142 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (120 mg, 0.374 mmol) and triethylamine (100 mg, 0.137 mL, 0.988 mmol) were combined with DMF (4 mL). The reaction mixture was stirred at room temperature for 10 min. After this time, 3-(aminomethyl)-7-chloro-N,N-dimethyl-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxamide (intermediate C) (0.052 g, 0.156 mmol) was added. The reaction mixture was stirred at room temperature for 15 hr. The crude material was purified by flash chromatography (10% ethyl acetate-hexanes ramped to 100% ethyl acetate). MS calcd. for C29H28ClN5O4 [(M+H)+] 546.2, obsd. 546.0.

Provenance & Evidence