1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67199240, compound

Participants

Reaction Conditions

Reaction Steps

Compound D2 (111 mg, 0.4 mmol), EDCl (155 mg, 0.72 mmol) and DMAP (174 mg, 1.44 mmol) in N-methyl pyrrolidinone (5 mL) was stirred 5 min at 20° C. N4-(4-Aminophenyl)-N6,N6-dimethyl-4,6-quinolinediamine (100 mg, 0.36 mmol) was then added and the reaction mixture was stirred at 20° C. for 20 h. The reaction mixture was diluted with water and stirred. The resulting precipitate was filtered washed with water and air dried. This solid was dissolved in hot MeOH, boiled with charcoal and filtered through a pad of celite. The filtrate was evaporated to dryness and the resulting residue was dissolved in MeOH (10 mL), 1.25 M HCl in MeOH (1 mL) was added and stirred 10 min. The solvent was evaporated and the residue was recrystallized from MeOH/EtOAc to give Cpd. HH (135 mg, 65%) as a yellow solid; m.p. (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 14.10 (br, 1H, N+H), 12.75 (br, 1H, N+H), 10.85 (br, 1H, NH), 10.45 (s, 1H, NH), 10.40 (s, 1H, NH), 8.27 (d, J=6.8 Hz, 1H, ArH), 8.08-7.99 (m, 6H, ArH), 7.88 (d, J=9.4 Hz, 1H, ArH), 7.65 (dd, J=9.4, 2.5 Hz, 1H, ArH), 7.54 (d, J=2.4 Hz, 1H, ArH), 7.45 (d, J=8.9 Hz, 2H, ArH), 6.67 (d, J=6.8 Hz, 1H, ArH), 6.27 (s, 1H, ArH), 3.12 [s, 6H, N(CH3)2], 2.32 (s, 3H, CH3); mass APCl+505.

Provenance & Evidence