[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH:4]=[CH:3][N:2]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:18][O:17][N:16]([CH3:15])[C:11]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:1]=[N:2][CH:3]=[CH:4]2)=[O:13]Commercially available isoquinoline-8-carboxylic acid (0.4 g, 2.31 mmol), N,O-dimethylhydroxylamine hydrochloride (0.45 g, 4.62 mmol), DMAP (0.28 g, 2.31 mmol), and polymer-supported DCC (0.71 g, 3.46 mmol) were charged in a 50 mL round bottom flask. Then anhydrous THF (23 mL) was added. The reaction was stirred overnight at RT. The reaction mixture was filtered and filtrate was concentrated. Purification by normal phase chromatography (0-50% EtOAc in hexane) yielded N-methoxy-N-methylisoquinoline-8-carboxamide (14-2).
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