Dichloromethane → HCID 68292186, compound

Participants

Reaction Steps

A 1.0 M dichloromethane solution of titanium(IV) chloride (0.025 mL, 0.025 mmol) was added to a solution of triethylamine (0.042 mL, 0.298 mmol) and benzylamine (6.39 mg, 0.060 mmol) in benzene (5 mL) at room temperature. The mixture was heated to reflux. A solution of 4-((2,2-dimethyl-3-oxocyclopentyl)amino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide (18 mg, 0.050 mmol, from Example 144) in benzene (1 mL) was added to the above mixture. The resultant mixture was kept at reflux for 3 h, cooled to room temperature, diluted with ethyl acetate (80 mL), washed with water, brine, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography, eluting with 30 to 80% ethyl acetate in hexanes, to give 4-(3-(benzylimino)-2,2-dimethylcyclopentylamino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide (7 mg, 31% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 10.66 (1 H, d, J=8.80 Hz), 7.80-8.02 (2 H, m), 7.55-7.76 (2 H, m), 7.20-7.53 (8 H, m), 7.10 (1 H, d, J=1.76 Hz), 5.59 (2 H, br. s.), 4.41-4.51 (1 H, m), 2.56-2.78 (1 H, m), 2.34-2.60 (2 H, m), 1.92-2.01 (1 H, m), 1.19-1.43 (6 H, m); MS (ES+) m/z: 452.3 (M+H).

Provenance & Evidence