[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([NH:17][CH2:18][CH2:19][O:20][CH3:21])[CH:5]=1.C=O.[BH3-][C:26]#N.[Na+]>C(O)(=O)C.CO>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]2)=[C:6]([N:17]([CH2:18][CH2:19][O:20][CH3:21])[CH3:26])[CH:5]=1To a solution of 170 mg of 3-(2-methoxy-ethylamino)-4-(4-methyl-piperazin-1-yl)-benzoic acid methyl ester (0.55 mmol, 1 eq.) in 5 mL of acetic acid were added 3 mL of aqueous solution of formaldehyde and the resulting mixture stirred for 10 minutes at room temperature; a solution of NaCNBH3 (680 mg, 11 mmol, 20 eq.) in 3 mL of MeOH was then added at 0° C. and the solution stirred for 5 minutes. The solvent was removed and the crude washed with water and dichloromethane. The combined organic layers were evaporated and the crude was purified by flash column chromatography, using dichloromethane-methanol 95:5 as eluant, affording 150 mg of the desired product.
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