[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1.C(N(CC)CC)C.[CH3:32][O:33][C:34](=[O:37])[CH2:35]Br>C1COCC1.CCOC(C)=O>[CH3:32][O:33][C:34](=[O:37])[CH2:35][N:12]([CH2:11][C:7]1[N:6]([CH2:5][C:4]2[CH:21]=[C:22]([Cl:24])[CH:23]=[C:2]([Cl:1])[CH:3]=2)[CH:10]=[CH:9][N:8]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1To a solution of [1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amine (200 mg, 0.55 mmol) and triethylamine (0.18 mL, 1.37 mmol) in THF (2 mL) was added methylbromoacetate (78 uL, 0.82 mmol). The reaction was stirred at ambient temperature for 18 h before diluting with EtOAc (50 mL). The solution was washed with water (20 mL) and brine then dried over Na2SO4. The solvent was removed in vacuo and the residue purified by column chromatography (silica gel, 5% MeOH in CH2Cl2). The purified product was treated with excess 2N HCl in Et2O solution to afford the hydrochloride salt of the desired product 7e (74 mg, 26%): ESI MS m/z 436 [C21H20Cl2FN3O+H]+.
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