1-Methylpiperazine → 1-methyl-8-{3-[(4-methylpiperazin-1-yl)methyl]phenoxy}-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

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Reaction Steps

To a solution of 8-(3-formylphenoxy)-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide 30 mg (0.086 mmol) in N,N-dimethylformamide (2 ml) and acetic acid (50 μl), N-methyl piperazine (13 μl, 0.13 mmol), and sodium cyanoborohydride (6 mg, 0.26 mmol) were added. The solution was stirred at r.t. for 3 hours, monitored by both TLC and LC/MS (method 1). The reaction was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4 filtered and concentrated. The residue was purified by column (DCM/MeOH/NH4OH 95/5/0.1) to give 1-methyl-8-{3-[(4-methylpiperazin-1-yl)methyl]phenoxy}-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide as major (15 mg 40%) LC/MS (254 nm) HPLC method 2 Rt 4.14 min. 1H NMR (401 MHz, DMSO-d6) δ 9.60 (s, 1H), 8.23 (d, J=8.79 Hz, 1H), 7.83 (s, 1H), 7.78 (d, J=8.79 Hz, 1H), 7.49-7.50 (m, 1H), 7.46 (t, J=7.81 Hz, 1H), 7.26 (dt, J=1.71, 7.69 Hz, 3H), 4.27 (s, 3H), 3.53 (s, 2H), 2.30-2.47 (m, 8H), 2.17 (br. s., 3H). HRMS (ESI) calcd for C23H25N7O2 [M+H]+ 432.2143 found 432.2141; and

Provenance & Evidence