Binap, (A+-)- → HCID 58711965, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (Example 9) (40 mg, 0.085 mmol), 4-[(4-methylpiperazin-1-yl)methyl]aniline (20.9 mg, 0.102 mmol), (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl ((S)-BINAP) (15.9 mg, 0.026 mmol), Tris(dibenzylidineacetone)dipalladium (0) (7.8 mg, 0.008 mmol) and sodium t-butoxide (11.4 mg, 0.12 mmol) was added 1,4-dioxane (1.5 mL). In a sealed reaction vessel, the mixture was heated with microwave radiation at 140° C. for 60 minutes. After cooling to room temperature, diluted mixture with methanol (5 mL) and ethyl acetate (5 mL) followed by filtration over celite. Removed solvent under reduced pressure and diluted brown residue in DMSO (1.0 mL). Injected (2×0.5 mL) on an Agilent reverse phase prep LC subjected to a gradient elution using acetonitrile(0.1% Formic acid):water(0.1% Formic acid) (10:90 to 90:10). The appropriate fractions were combined and concentrated under reduced pressure to give 5-methyl-7-[3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)phenyl]-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.021 g) as a yellow solid. 1H NMR (CDCl3): δ8.78 (s, 1H), 8.47 (s, 1H), 8.09 (dd, J=1.9, 1.8 Hz, 1H), 8.0-7.98 (m, 1H), 7.33 (dd, J=7.9, 7.8 Hz, 1H), 7.19 (ddd, J=7.9, 2.2, 0.8 Hz, 1H), 7.16-7.14 (m, 2H), 7.11 (s, 1H), 7.07-7.05 (m, 2H), 6.94 (m, 2H), 3.82 (s, 9H), 3.53 (s, 2H), 2.90-2.54 (m, 14H). MS m/z 595 (M+1).

Provenance & Evidence