Hydrochloric Acid → 3-[(2,6-diamino-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of amine B6 (204 mg, 0.55 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloro-6-nitroquinoline (126 mg, 0.61 mmol) and stirred until it dissolved, then 2 drops of c.HCl was added. The reaction mixture was refluxed for 4 h, diluted with EtOAc, brought to boil and cool to 20° C. The resulting precipitate was filtered and recrystallized from MeOH/EtOAc to give Cpd. RRR1 (224 mg 70%); m.p. (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 14.75 (br, 1 H, N+H), 11.50 (br, 1 H, N+H), 11.10 (br, 1 H, NH), 10.50 (s, 1 H, NH), 9.88 (s, 1 H, NH), 9.77 (s, 1 H, NH), 9.76 (s, 1 H, ArH), 8.66 (d, J=9.3 Hz, 1 H, ArH), 8.60 (d, J=6.8 Hz, 1 H, ArH), 8.19 (d, J=9.3 Hz, 1 H, ArH), 8.25 (d, J=8.8 Hz, 2 H, ArH), 7.94 (br s 2 H, NH2), 7.71 (d, J=7.6 Hz, 1 H, ArH), 7.56-7.42 (m, 6 H, NH2 & 4×ArH), 6.91 (d, J=6.8 Hz, 1 H, ArH), 5.44 (s, 1 H, ArH). HRMS (FAB+) calc. for C26H22N9O3 (M+1) m/z 508.1846, found 508.1841.

Provenance & Evidence