(4-Fluoro-3-methylphenyl)methanamine → HCID 54747151, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 10-(((dimethylamino)(oxo)acetyl)(methyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate (3 g, 7.65 mmol) in ethanol (80 mL) was added (4-fluoro-3-methylphenyl)methanamine (2.90 mL, 22.94 mmol) and the mixture was heated at 90° C. for 18 h. The reaction mixture was cooled, concentrated, diluted with ethyl acetate and washed twice with 0.2N NaOH (2×100 mL). The organic layer was discarded and the aqueous layer acidified with conc. HCl and extracted with dichloromethane (2×150 mL), dried (Na2SO4), filtered and concentrated. The crude product was recrystallized from methanol to afford the title compound (2.5 g, 66% yield) as a crystalline white solid. 1H NMR (500 MHz, CDCl3) δ: 12.13 (1 H, s), 9.56 (1 H, brs), 7.20-7.23 (1 H, m), 7.15-7.20 (1 H, m), 6.88-6.93 (1 H, m), 4.83 (1 H, dd, J=15.56, 7.02 Hz), 4.55-4.62 (1 H, m), 4.39-4.45 (1 H, m), 3.60 (1 H, d, J=15.56 Hz), 3.33-3.47 (2 H, m), 3.01 (3 H, s), 2.99 (3H, s), 2.97 (3 H, s), 2.49 (1 H, brs), 2.23 (3 H, d, J=1.83 Hz), 1.97-2.09 (4 H, m), 1.74-1.84 (2 H, m). LCMS (M+H)=500.69. HPLC purity: >95%.

Provenance & Evidence