[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1[Cl:26].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:26][C:16]1[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][C:15]=1[NH:14][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1)=[O:13]
In DMF (15 ml) were dissolved 1-isoquinolinecarboxylic acid (1.00 g, 5.77 mmol), methyl 4-amino-3-chlorophenylacetate (1.23 g, 6.16 mmol), HOBt (0.16 g, 1.15 mmol), and DMAP (0.14 g, 1.15 mmol). To the resulting solution was added EDC HCl (1.33 g, 6.93 mmol), followed by stirring at room temperature for 14 hours. The reaction mixture was poured into water (40 ml). The crystals precipitated were collected by filtration under reduced pressure, washed with water and ether, dried under reduced pressure to give methyl (3-chloro-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate (1.14 g, 56%) as a brown solid.
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