Reaction Steps
To a solution of compound B6 (150 mg, 0.37 mmol) in EtOH (15 mL) and H2O (7.5 mL) was added 4-chloroquinoline (73 mg, 0.45 mmol) and stirred until it dissolved, then 2 drops of c.HCl was added. The reaction mixture was refluxed for 20 h, diluted with EtOAc, brought to boil and cool to 20° C. The resulting precipitate was filtered and stirred in aqueous NH3 (20 ml) to convert to free base. This new precipitate was filtered and chromatographed (neutral Al2O3, 0-7% DCM/MeOH) to give pure free base of the product. This was then converted to HCl salt by using 1.25 M HCl in MeOH to give Cpd. FF2 (139 mg, 70%); m.p (MeOH/EtOAc)>300° C. 1H NMR [(CD3)2SO] δ14.25 (br, 1 H, N+H), 12.00 (br, 1 H, N+H), 10.95 (s, 1 H, NH), 10.53 (s, 1 H, NH), 9.93 (s, 1 H, NH), 9.05 (d, J=8.5 Hz, 1 H, ArH), 7.51 (d, J=7.0 Hz, 1 H, ArH), 8.06-8.00 (m, 5 H, ArH), 7.95-7.91 (br m, 2 H, NH2), 7.81 (d d, J=7.6, 1.4 Hz, 1 H, ArH), 7.71 (d, J=7.6 Hz, 1 H, ArH), 7.58 (s, 2 H, NH2), 7.57-7.47 (m, 5 H, ArH), 6.78 (d, J=7.0 Hz, 1 H, ArH), 6.78 (d, J=7.0 Hz, 1 H, ArH), 5.46 (s, 1 H, ArH); HRMS (FAB+) calc. for C26H23N8O (M+1) m/z 463.1995, found 463.1992.
