[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>CN(C=O)C.O>[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)=[O:12])[CH2:38][CH2:37]1
Indole-5-carboxylic acid (4.09 g, 25.4 mmol) was dissolved in DMF (200 mL), and the solution was added with EDCI (9.74 g, 50.8 mmol) and HOBT monohydrate (1.95 g, 12.7 mmol) under ice-cooling, followed by stirring at the same temperature for 10 minutes. Then, the reaction mixture was added with N-methylpiperazine (8.45 mL, 76.2 mmol), followed by stirring at room temperature for 3.7 hours. The reaction mixture was added with water and extracted with ethyl acetate and chloroform. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=100/0, 90/10) to obtain 5-(4-methylpiperazin-1-ylcarbonyl)indole (5.81 g, yield 94%).
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