(4-chloro-2-(dimethylamino)-3-phenylquinolin-6-yl)(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanol → 4-Chloro-6-((4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-N,N-dimethyl-3-phenylquinolin-2-amine

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Reaction Conditions

Reaction Steps

To (4-chloro-2-(dimethylamino)-3-phenylquinolin-6-yl)(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanol (83.6 mg, 0.166 mmol, Example 90) in NMP (1.5 mL), was added copper (I) cyanide (16.4 mg, 0.183 mmol). The mixture was heated by microwave irradiation for 10 minutes at 120° C. The mixture was partitioned between MTBE and saturated aqueous NH4OH. The organic phase was washed with water. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by RP-HPLC (10-90% CH3CN—H2O, 0.1% TFA) and fractions were converted to the corresponding free base by extraction from saturated aqueous NaHCO3 with DCM. Further purification by flash column chromatography (silica gel, 10-70% acetone-DCM) afforded the title compound. 1H NMR (400 MHz, CDCl3) δ 7.82 (d, J=1.96 Hz, 1H), 7.76 (d, J=8.80 Hz, 1H), 7.55 (br. s., 1H), 7.43-7.50 (m, 2H), 7.34-7.42 (m, 4H), 7.30 (d, J=8.56 Hz, 2H), 7.12 (d, J=8.56 Hz, 2H), 6.48 (br. s., 1H), 5.45 (s, 1H), 3.37 (s, 3H), 2.71 (s, 6H); MS m/e 487.0 (M+H)+.

Provenance & Evidence