Hydrochloric Acid → 4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(7-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of C3 (235 mg, 0.58 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloro-7-nitroquinoline (132 mg, 0.63 mmol) and stirred until it dissolved, then 2 drops of c.HCl was added. The reaction mixture was refluxed for 5 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. GG5 (317 mg 94%) as a yellow solid.; m.p (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ12.9 (br, 1 H, N+H), 10.81 (brs, 2H, 2×NH), 10.44 (s, 1 H, NH), 8.93 (d, J=9.3 Hz, 1 H, ArH), 8.81 (d, J=1.9 Hz, 1 H, ArH), 8.66 (d, J=6.6 Hz, 1 H, ArH), 8.46 (d, J=8.9 Hz, 1 H, ArH), 8.05-7.98 (m, 8 H, ArH & NH2), 7.47 (d, J=8.8 Hz, 1 H, ArH), 6.94 (d, J=6.6 Hz, 1 H, ArH), 6.26 (s, 1 H, ArH), 2.32 (s, 3 H, CH3); HRMS (FAB+) calc. for C27H23N8O3 (M+1) m/z 507.1893, found 507.1885.

Provenance & Evidence