[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6])#[CH:2].[CH:12]1C=CC2N(O)N=NC=2C=1.Cl.[NH:23]1[CH2:31][CH2:30][CH:26]([C:27]([OH:29])=O)[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][C:27]([CH:26]2[CH2:25][CH2:24][N:23]([CH3:12])[CH2:31][CH2:30]2)=[O:29])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])#[CH:2]3-Ethynyl-4-methoxyaniline (300 mg, 2 mmol) in DCM (20 mL) was treated in a subsequent manner with HOBt (351 mg, 2.6 mmol), isonipecotic acid hydrochloride (467 mg, 2.6 mmol), DIPEA (906 μL, 5.2 mmol) and finally EDCl (498 mg, 2.6 mmol). The reaction was stirred at room temperature for 1.5 h. The organic phase was washed with saturated sodium hydrogen carbonate solution and dried over sodium sulfate. Evaporation of the solvent left a brownish solid which was employed in the following reaction without further purification.
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