[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Cl.Cl.[NH2:17][CH2:18][C:19]1[CH:20]=[C:21]([CH:36]=[CH:37][CH:38]=1)[C:22]([NH:24][C:25]1[CH:34]=[C:33]2[C:28]([CH2:29][CH2:30][N:31]([CH3:35])[CH2:32]2)=[CH:27][CH:26]=1)=[O:23].C(N(CC)CC)C>CN(C=O)C.O.FC(F)(F)C(O)=O>[CH3:35][N:31]1[CH2:30][CH2:29][C:28]2[C:33](=[CH:34][C:25]([NH:24][C:22]([C:21]3[CH:20]=[C:19]([CH:38]=[CH:37][CH:36]=3)[CH2:18][NH:17][C:10](=[O:12])[C:9]3[CH:8]=[CH:7][C:6]([N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)=[CH:14][CH:13]=3)=[O:23])=[CH:26][CH:27]=2)[CH2:32]1Dissolve 4-[1,2,4]triazol-1-yl-benzoic acid (29 mg, 0.15 mmol) and CDI (N,N′-carbonyldiimidazole) (25 mg, 0.15 mmol) in DMF (2 mL) and stir the mixture for 1 h. To this add 3-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide dihydrochloride (50 mg, 0.14 mmol) and triethylamine (0.095 mL, 0.68 mmol) and stir the mixture overnight. Dilute the mixture with water (1 mL) and trifluoroacetic acid (0.2 mL) and purify by prep-HPLC (5%-70%, CH3CN/H2O) to give the desired product 4-[1,2,4]triazol-1-yl-benzoic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (51 mg, 0.086 mmol). MS, electrospray 467.4 (M+H), rt 1.05 min.
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