Diisopropylethylamine → HCID 71208437, compound

Participants

Reaction Conditions

Reaction Steps

In a 50 mL flask, 3-aminomethyl-7-chloro-1-phenyl-1H-quinolin-4-one hydrochloride salt (intermediate I) (50 mg, 0.132 mmol) and morpholine-4-carbonyl chloride (21.7 mg, 0.145 mmol) were combined with CH2Cl2 (5 mL) and stirred at 0° C. for 10 min. Then N,N-diisopropylethylamine was added at 0° C. over 1 hr. The reaction mixture was stirred at and stirred at 0° C. for 4 hr. The reaction mixture was concentrated. The crude product was purified using preparative reverse phase HPLC to yield the product 7-chloro-3-{[(morpholine-4-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quino-line-2-carboxylic acid methyl ester. MS calcd. for C23H23ClN3O5 [(M+H)+] 456.1, obsd. 455.9.

Provenance & Evidence