2-Chlorobenzothiazole → HCID 71486684, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (40 mg, 0.140 mmol), N,N-diisopropylethylamine (74.0 mg, 100 μL, 0.567 mmol) and 2-chlorobenzothiazole (31 mg, 0.181 mmol) in NMP (0.5 mL) was heated at 115° C. in a sealed tube. After 2 hr., LCMS indicated the desired product to be present with some remaining starting material and minor impurities. Heating continued overnight. In the morning, more 2-chlorobenzothiazole (12 mg, 0.070 mmol) was added. Heating continued for another 24 hr. The reaction mixture was concentrated under a stream of nitrogen, and the crude product was purified by preparative reverse phase HPLC. The desired product 3-(benzothiazol-2-ylaminomethyl)-7-chloro-1-phenyl-1H-quinolin-4-one (13 mg, 22%) was obtained an off-white solid. MS calcd. for C23H16ClN3OS [(M+H)+] 418.1, obsd. 418.

Provenance & Evidence