106860-19-9

Basic information

• Product Name: 6H-Pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 9-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-, 1,1-dimethylethyl ester, (1S,9S)-
• CAS NO: 106860-19-9
• Molecular Formula: C26H39N3O5
• Molecular Weight: 473.613
• Mol File: 106860-19-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 6H-Pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 9-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-, 1,1-dimethylethyl ester, (1S,9S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 9-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-, 1,1-dimethylethyl ester, (1S,9S)-(106860-19-9)
• EPA Substance Registry System: 6H-Pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 9-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-, 1,1-dimethylethyl ester, (1S,9S)-(106860-19-9)

Safety Data

• Hazardous Substances Data: 106860-19-9(Hazardous Substances Data)

Upstream product

• 109010-59-5 (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester 
• 106860-20-2 9-amino-octahydro-10-oxo-6H-pyridazo[1,2-a][1,2]diazepine-1-(S)carboxylic acid t-butyl ester 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 603-35-0 triphenylphosphine 
• 88784-33-2 (2S)-4-benzyloxicarbonyl-2-phthalimidobutanoic acid 
• 106928-72-7 (1S,9S)-t-butyl 1,2,3,4,7,8,9,10-octahydro-6,10-dioxo-9-phthalimidopyridazino<1,2-a><1,2>diazepine-1-carboxylate 
• 106927-97-3 (1S,9S)-t-butyl octahydro-10-oxo-9-phthalimido-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate 
• 72064-51-8 (3S)-N¹-benzyloxycarbonyl-piperazic acid tert-butyl ester 
• 106860-13-3 (S)-2-[(S)-4-Benzyloxycarbonyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyryl]-tetrahydro-pyridazine-1,3-dicarboxylic acid 1-benzyl ester 3-tert-butyl ester 
• 88767-18-4 (S,S)-5-(6-(tert-butoxycarbonyl)tetrahydropyridazin-1(2H)-yl)-4-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid 
• 88767-16-2 (S)-4-Chlorocarbonyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid benzyl ester 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 88767-98-0 ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate 

Downstream Products

• 88768-40-5 cilazapril 

Relevant articles and documents

Synthesis method of cilazapril containing hexahydropyridazine acid structure

The invention discloses a simple synthesis method of cilazapril containing a hexahydropyridazine acid structure. (1S,9S)-9-amino-10-oxo-6H-pyridazine[1,2-a][1,2]diazepine-1-carboxylic acid tert-butylester(II) and (R)-2-hydroxy phenyl butyrate ethyl ester(III) are subjected to a Mitsunobu condensation reaction at 0-60 DEG C and under the action of triphenylphosphine and azodicarboxylate to form amixture of (1S,9S)-9-[(1S)-ethoxycarbonyl-3-phenylpropylamino]octahydro-10-oxo-6H-pyridazine[1,2-a][1,2]diazepine-1-carboxylic acid tert-butyl ester(IV) and (1S,9S)-9-[[(1S)-ethoxycarbonyl-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazine[1,2-a][1,2]diazepine-1-carboxylic acid tert-butyl ester triphenylphosphine salt(V), crude cilazapril is prepared from the mixture under the action of an aqueous hydrochloric acid solution, and then the crude cilazapril is recrystallized to obtain cilazapril (I). By adopting the synthesis method provided by the invention, a step of purification operation isreduced, the operation is simple, the use of expensive trifluoromethanesulfonic anhydride and pyridine with an unpleasant odor is avoided, and the method is suitable for industrial production.

A NOVEL PROCESS FOR THE PREPARATION OF CILAZAPRIL

Cilazapril is prepared in good yield using ethyl R-2-(nitro or halo substituted benzene sulfonyloxy)-4-phenyl butyrate. Thus, (1S,9S)-t-butyl octahydro-10-oxo-9-amino-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate is reacted with ethyl R-2-(4-nitro benz