819793-75-4

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 59467-62-8 7-chloro-5-(2-fluorophenyl)-2-(N-nitrosomethylamino)-3H-1,4-benzodiazepine 
• 2886-65-9 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2(2H)-one 
• 784-38-3 2-amino-5-chloro-2'-fluorobenzophenone 
• 1584-62-9 2?(2?bromoacetamido)?5?chloro?2'?fluorobenzophenone 
• 59467-61-7 [7-chloro-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-ylidene]-methyl-amine 
• 1645-32-5 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepine-2-thione 

Downstream Products

• 819793-80-1 8?chloro?6?(2?fluorophenyl)?1?methyl?3?(4?toluenesulfonyl)?4H?imidazo[1,5?a][1,4]benzodiazepine 
• 59467-70-8 Midazolam 

Relevant academic research and scientific papers

Improved and scalable methods for the synthesis of midazolam drug and its analogues using isocyanide reagents

Abstract: In this research, two improved and scalable methods for the synthesis of midazolam and its analogues have been described. Midazolam has been synthesized using isocyanide reagents in satisfactory yield. In this methodology, imidazobenzodiazepine intermediates can be easily prepared via an improved process. One-pot condensation of benzodiazepines with mono-anion of tosylmethyl isocyanide or ethyl isocyanoacetate under mild condition led to formation of imidazobenzodiazepine. In the first method, tosylmethyl isocyanide (Tos-MIC) is used and the number of synthetic steps are decreased in comparison to previous report. In the second method, ethyl isocyanoacetate which is commonly used for the synthesis of some imidazobenzodiazepines, is consumed to generate midazolam. The latter, a relatively different method for the synthesis of midazolam analogues has been reported. Graphical abstract: [Figure not available: see fulltext.].

Reactions of 1,4-benzodiazepinic N-nitrosoamidines with tosylmethyl isocyanide: A novel synthesis of midazolam

Reaction of 1,4-benzodiazepinic N-nitrosoamidines, used as synthetic equivalents of imidoyl chlorides, with the monoanion of tosylmethyl isocyanide is described. The process gives entry to 3-(4-tosyl)imidazo[1,5-a][1,4] benzodiazepines, compounds which have not been described yet in the literature. These systems can be derivatized to the corresponding trisubstituted 1,4-benzodiazepines by alkylation or acylation of the imidazole ring. These new heterocyclic derivatives are potentially useful in the field of medicinal chemistry. In addition, midazolam 3, the anesthetic properties of which are well established, can be easily prepared in one step by desulfonylation of compound 7a.