1-Methylpiperazine → 4-tert-Butyl-N-(3-(6-(4-(1-(isopropyl(methyl)amino)-2-(4-methylpiperazin-1-yl)-2-oxoethyl)phenylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl)benzamide

Participants

Reaction Steps

To a sealed tube equipped with a magnetic stirrer, were charged 29 (100 mg, 0.168 mmol), 1-methylpiperazine (14.6 mg, 0.168 mmol), DMF (3 mL), Hunig's base (65.1 mg, 0.503 mmol), and BOP (74.3 mg, 0.168 mmol). The reaction mixture was stirred at room temperature for 26 hrs. Most solvent was removed by rotary evaporation and the resulting residue was dissolved in ethyl acetate (100 mL). The solution was washed with water (15 mL×3), dried over MgSO4, filtered and solvent removed in vacuo. Silica gel column chromatography (MeOH:CH2Cl2=5:95) afforded 30 as a light yellow solid, 25 mg (22%). 1H NMR (300 MHz, CDCl3) 8.45 (s, 1H), 8.09 (s, 1H), 7.95 (s, 1H), 7.92 (s, 1H), 7.85 (m, 2H), 7.75 (m, 1H), 7.54 (s, 1H), 7.51 (s, 1H), 7.40 (m, 2H), 7.19-7.23 (m, 2H), 6.79 (s, 1H), 5.19 (s, 1H), 3.62 (s, 3H), 3.40 (broad s, 2H), 3.21 (broad s, 2H), 2.26-2.50 (m, 9H), 2.18 (s, 3H), 1.92 (broad s, 2H), 1.34 (s, 9H), 1.25-1.31 (m, 6H) ppm; MS (ESI+) m/z 678.19 (M+H).

Provenance & Evidence