CILAZAPRIL

Base Information

• Chemical Name: CILAZAPRIL
• CAS No.: 106860-20-2
• Molecular Formula: C22H33N3O6
• Molecular Weight: 283.371
• Mol file: 106860-20-2.mol

Synonyms:beta-Alanine, N-[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-, ethyl ester;6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 9-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-, (1S,9S)-, hydrate (1:1);(1S,9S)-9-{[(2S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid hydrate (1:1);[1S-[1a,9a(R*)]]-9-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic Acid Monohydrate;

Chemical Property of CILAZAPRIL

Chemical Property:

• Boiling Point: 598.1 °C at 760 mmHg
• PKA: 8.57±0.40(Predicted)
• Flash Point: 315.5 °C
• PSA: 108.41000
• Density: 1.17
• LogP: 1.79790

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CILAZAPRIL

There total 8 articles about CILAZAPRIL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1S,9S)-t-butyl octahydro-10-oxo-9-phthalimido-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate (106927-97-3) → 9-amino-octahydro-10-oxo-6H-pyridazo[1,2-a][1,2]diazepine-1-(S)carboxylic acid t-butyl ester (106860-20-2)

Guidance literature:

With hydrazine hydrate; In ethanol; for 1h; Ambient temperature;

Reference yield:

(S)-4-Chlorocarbonyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid benzyl ester (88767-16-2) → 9-amino-octahydro-10-oxo-6H-pyridazo[1,2-a][1,2]diazepine-1-(S)carboxylic acid t-butyl ester (106860-20-2)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃ / toluene; H₂O / 17 h / Ambient temperature

2: H₂ / 5percent Pd-C / dimethylformamide / 18 h

3: SOCl₂ / CH₂Cl₂ / 4 h / Ambient temperature

4: 90 percent / 1M borane in THF / tetrahydrofuran / 3 h / Ambient temperature

5: hydrazine hydrate / ethanol / 1 h / Ambient temperature

With thionyl chloride; borane-THF; hydrogen; sodium hydrogencarbonate; hydrazine hydrate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

(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 (106860-13-3) → 9-amino-octahydro-10-oxo-6H-pyridazo[1,2-a][1,2]diazepine-1-(S)carboxylic acid t-butyl ester (106860-20-2)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 5percent Pd-C / dimethylformamide / 18 h

2: SOCl₂ / CH₂Cl₂ / 4 h / Ambient temperature

3: 90 percent / 1M borane in THF / tetrahydrofuran / 3 h / Ambient temperature

4: hydrazine hydrate / ethanol / 1 h / Ambient temperature

With thionyl chloride; borane-THF; hydrogen; hydrazine hydrate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(1S,9S)-t-butyl octahydro-10-oxo-9-phthalimido-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate

(S)-4-Chlorocarbonyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid benzyl ester

(S,S)-5-(6-(tert-butoxycarbonyl)tetrahydropyridazin-1(2H)-yl)-4-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid

(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

Downstream raw materials:

(1S,9S)-t-butyl 9-<(1S)-ethoxycarbonyl-3-phenylpropylamino>octahydro-10-oxo-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate

cilazapril

Refernces

• 1、 Attwood, Michael R.,Hassall, Cedric H.,Kroehn, Antonin,Lawton, Geoffrey,Redshaw, Sally. "The Design and Synthesis of the Angiotensin Converting Enzyme Inhibitor Cilazapril and Related Bicyclic Compounds". . p. 1011 - 1020. Retrieved 2007/10/02.