N-(7-Chloro-4-quinolinyl)-N'-[2-[(7-chloro-4-quinolinyl)aMino]ethyl]-1,2-ethanediaMine synthesis

Yield:215592-20-4 55%

Reaction Conditions:

at 80 - 130; for 8 h;

Steps:

Synthesis of BAQ.

4,7-dichloroquinoline (1.2 g, 6.00 mmol) in a 10 mL flask was maintained at 80°C for 2 h without stirring, followed by adding diethylenetriamine (0.22 mL, 2.00 mmol). The reaction solution was stirred at 130°C for 6 h. The residue was taken up with 30 mL methanol to afford white solid as the BAQ compound. Yield: 470 mg, 55%.¹H NMR (600 MHz, DMSO-d₆): d 8.38 (d, 2 H, J=6.0 Hz), 8.23 (d, 2 H, J=10.8 Hz), 7.78 (d, 2 H, J=1.8 Hz), 7.42 (dd, 2 H, J1=10.8 Hz, J2=2.4 Hz), 7.25 (s, 1 H), 6.51 (d, 2 H, J=6.6 Hz), 3.40 (t, 4 H, J=7.2 Hz), 2.94 (t, 4 H, J=7.8 Hz). ESI-HRMS: m/z [M+H]⁺ calcd for C₂₂H₂₂Cl₂N5⁺ 426.1247, found 426.1243.

References:

WO2021/55705,2021,A1 Location in patent:Paragraph 0154