proline dl-form → HCID 59375399, compound

Participants

Reaction Conditions

Reaction Steps

9-bromo-4-iodo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (50 mg, 0.10 mmol), sodium methanesulfinate (13.27 mg, 0.130 mmol), DL-proline (2.302 mg, 0.020 mmol), copper(I) iodide (1.904 mg, 10.00=01) and NaOH (0.800 mg, 0.020 mmol) were combined in a 2-dram vial that was then flushed with nitrogen and kept under a nitrogen atmosphere. DMSO (500 μl) was then added and the reaction was heated to 90° C. and stirred for 72 h. Then, the reaction was purified by preparative HPLC reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to give the title compound as a pale yellow solid. LRMS (ESI) calc'd for (C19H23BrN3O3S) [M+H]+ 452.1; found 452.0.

Provenance & Evidence