Morpholine → HCID 50906574, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of N-(5-bromo-2-morpholinopyridin-3-yl)-5,7-difluoro-N,3-dimethyl-2-(pyridin-2-yl)quinolin-4-amine (12.0 mg, 0.023 mmol), tris(dibenzylideneacetone)dipalladium (0) (2.1 mg, 2.280 μmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (2.2 mg, 4.56 μmol), and sodium tert-butoxide (15 mg, 0.153 mmol) in toluene (2 mL) was purged three times with argon and placed under vacuum three times. Before heating, morpholine (9.93 μL, 0.114 mmol) was added and the mixture was heated to 100° C. Stirring continued for 21 h. After which the reaction was cooled to rt, diluted with water and extracted with EtOAc (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was dissolved in MeOH and purified by HPLC (10-90% of 0.1% TFA acetonitrile solution in 0.1% TFA water solution) to yield N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,7-difluoro-N,3-dimethyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (400 MHz, CD3OD) δ ppm 8.66 (1H, d, J=4.7 Hz), 8.01 (1H, m), 7.78 (1H, d, J=7.8 Hz), 7.61-7.67 (1H, m), 7.60 (1H, d, J=2.7 Hz), 7.51 (1H, m), 7.23 (1H, m), 7.10 (1H, br. s.), 3.82-3.92 (4H, m), 3.35-3.44 (4H, m), 3.31 (4H, m), 3.17-3.28 (4H, m), 2.46 (3H, br. s.), 1.94-2.04 (3H, s); Mass Spectrum (ESI) m/e=533.2 (M+1).

Provenance & Evidence