470690-99-4Relevant articles and documents
Preparation of a clinically investigated ras farnesyl transferase inhibitor
Maligres, Peter E.,Waters, Marjorie S.,Weissman, Steven A.,McWilliams, J. Christopher,Lewis, Stephanie,Cowen, Jennifer,Reamer, Robert A.,Volante,Reider, Paul J.,Askin, David
, p. 229 - 241 (2007/10/03)
The synthesis of ras farnesyl-protein transferase inhibitor 1 is described on a multi-kilogram scale. Retrosynthetic analysis reveals chloromethylimidazole 2 and a piperazinone 3 as viable precursors. The 1,5-disubstituted imidazole system was regioselectively assembled via an improved Marckwald imidazole synthesis. A new imidazole dethionation procedure has been developed to convert the Marckwald mercaptoimidazole product to the desired imidazole. This methodology was found to be tolerant of a variety of functional groups providing good to excellent yields of 1,5-disubstituted imidazoles. A new Mitsunobu cyclization strategy was developed to prepare the arylpiperazinone fragment 3.
Syntheses of substituted pyrrolo[2,3-d]imidazole-5-carboxylates and substitued pyrrolo[3,2-d]imidazole-5-carboxylates
Shafiee,Mojarrad, J. Shabhbazi,Jalili,Adhami,Hadizadeh
, p. 367 - 373 (2007/10/03)
Starting from readily available p-substituted-benzylamines a series of ethyl 2-alkylthio-1-substituted-benzylpyrrolo[2,3-d]imidazole-5-carboxylates was prepared. In addition, starting from 2-alkyl-4(or 5)-formylimidazoles and methyl 4′-bromomethylbiphenyl-2-carboxylate a series of methyl substituted-pyrrolo[2,3-d]imidazole-5-carboxylates and methyl substituted-pyrrolo[3,2-d]imidazole-5-carboxylates was prepared.