C(OC(=O)[N:7]=[C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:22][CH2:21]2)[C:11]2[CH:39]=[CH:40][CH:41]=[CH:42][C:10]=2[N:9]1[CH2:43][CH2:44][CH2:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:28]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:23]1[CH2:22][CH2:21][N:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][N:12]2[C:11]3[CH:39]=[CH:40][CH:41]=[CH:42][C:10]=3[N:9]([CH2:43][CH2:44][CH2:45][O:46][C:47]3[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=3)[C:8]2=[NH:7])[CH2:25][CH2:24]1To [1-[2-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl ester (100 mg, 0.14 mmol) at rt was added 25% TFA in dichloromethane (5 ml). The reaction was stirred for 1 h and then concentrated under reduced pressure. The crude product was purified by preparative HPLC and then partitioned between saturated NaHCO3 and dichloromethane. The organic phase was separated, washed with H2O, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-[2-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (2.8 mg, 3%). HPLC-MS 626 [M+1]+, 324.
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