Borane → HCID 59631388, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-N,N-dimethyl-5-morpholinobenzamide (0.074 g, 0.152 mmol) in THF (1.5 mL) was added 1M borane:THF complex (0.76 mL, 0.762 mmol). The reaction was stirred at 60° C. for 18 h, then cooled to 23° C., quenched with 0.7 mL concd HCl, and concd. To the resulting residue, 5 mL water was added as the reaction was stirred at 90° C. for one hour. The reaction was then basified with 1M sodium hydroxide, and the product was extracted twice with EtOAc. The combined organics were dried over magnesium sulfate and concd, affording a crude material that was purified by reverse-phase HPLC (0-70% acetonitrile in water). This yielded N-(3-((dimethylamino)methyl)-5-(4-morpholinyl)phenyl)-7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.65-8.72 (1H, m), 8.47 (1H, s), 8.08 (1H, dd, J=9.2, 6.3 Hz), 7.96-8.01 (1H, m), 7.83-7.87 (1H, m), 7.69-7.73 (1H, m), 7.42-7.50 (2H, m), 6.38 (1H, s), 6.27-6.30 (1H, m), 6.09-6.11 (1H, m), 3.69 (4H, dd, J=5.6, 4.0 Hz), 3.23 (1H, br. s.), 2.99-3.05 (4H, m), 2.18 (3H, s), 2.10 (5H, br. s.). Mass Spectrum (ESI) m/e=472.2 (M+1).

Provenance & Evidence