2-Aminothiazole → 2-(2-(piperidin-4-yloxy)phenyl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

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The same general amide coupling procedure outlined above was used, employing 2-(2-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 27 and 2-aminothiazole 4 as the starting materials. The resulting crude amide coupling product (0.2 mmol) was treated with 4 mL of 25% TFA in CH2Cl2 and allowed to stand at room temperature for 8 h. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC using aqueous acetonitrile that has buffered with 0.1% TFA to afford 2-(2-(piperidin-4-yloxy)phenyl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide (Compound 428). MS (ESI) calcd for C22H21N5O2S: 419.14; found: 420 [M+H].

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