Hydrochloric Acid → 4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of compound C3 (200 mg, 0.49 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloro-6-nitroquinoline (113 mg, 0.54 mmol) and stirred until it dissolved, then 2 drops of c.HCl was added. The reaction mixture was refluxed for 3 h., diluted with EtOAc, brought to boil and cool to 20° C. The resulting precipitate was filtered and recrystallized from MeOH/EtOAc/Charcoal/Celite to give Cpd. GG4 (247 mg 87%) as a yellow solid.; M.P (MeOH/EtOAc) 295-300° C.; 1H NMR [(CD3)2SO] δ13.50 (br, 2 H, 2×N+H), 11.32 (br, 1 H, NH), 11.00 (brs, 1 H, NH), 10.51 (s, 1 H, NH), 9.81 (d, J=2.2 Hz, 1 H, ArH), 8.69 (dd, J=9.3, 2.2 Hz, 1 H, ArH), 8.59 (d, J=6.9 Hz, 1 H, ArH), 8.24 (d, J=9.3 Hz, 1 H, ArH), 8.06-7.98 (m, 7H, ArH & NH2), 7.48 (d, J=8.9 Hz, 2 H, ArH), 6.90 (d, J=6.9 Hz, 1 H, ArH), 6.32 (s, 1 H, ArH), 2.32 (d, J=0.4 Hz, 3 H, CH3); HRMS (FAB+) calc. for C27H23N8O3 (M+) m/z 507.1893, found 507.1896.

Provenance & Evidence