Saprisartan

Base Information

• Chemical Name: Saprisartan
• CAS No.: 146623-69-0
• Molecular Formula: C25H22 Br F3 N4 O4 S
• Molecular Weight: 611.439
• UNII: HS64NG1G69
• DSSTox Substance ID: DTXSID00163422
• Nikkaji Number: J608.584I
• Wikidata: Q20817193
• NCI Thesaurus Code: C152297
• Metabolomics Workbench ID: 43509
• ChEMBL ID: CHEMBL305544
• Mol file: 146623-69-0.mol

Synonyms:GR 138950;GR-138950;GR138950;GR138950C;sapri-sartan potassium;saprisartan potassium

Chemical Property of Saprisartan

Chemical Property:

• Vapor Pressure: 7.48E-20mmHg at 25°C
• Boiling Point: 707.3°Cat760mmHg
• Flash Point: 381.5°C
• PSA: 128.60000
• Density: 1.7g/cm³
• LogP: 7.76140
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 610.04972
• Heavy Atom Count: 38
• Complexity: 979

Purity/Quality:

98%min ^*data from raw suppliers

Saprisartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=NC(=C(N1CC2=CC3=C(C=C2)OC(=C3Br)C4=CC=CC=C4NS(=O)(=O)C(F)(F)F)C(=O)N)C5CC5
• Uses: Antihypertensive. Saprisartan is an angiotensin AT1 receptor antagonist with antihypertensive effects .

Technology Process of Saprisartan

There total 17 articles about Saprisartan 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:

1,1'-carbonyldiimidazole (530-62-1) + 1-<<3-bromo-2-<2-<<(trifluoromethyl)sulfonyl>amino>phenyl>-5-benzofuranyl>methyl>-4-cyclopropyl-2-ethyl-1H-imidazole-5-carboxylic acid (146623-68-9) → saprisartan (146623-69-0)

Guidance literature:

With hydrogenchloride; ammonia; In tetrahydrofuran;

Reference yield:

3-Cyclopropyl-2-nitro-3-oxo-propionic acid ethyl ester (1025993-01-4) → saprisartan (146623-69-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 60 percent / H₂, AcCl / 5percent Pd/C / ethanol / 5 h / 760 Torr / Ambient temperature

2: 24 percent / Et₃N / ethanol

3: 62 percent / K₂CO₃ / dimethylformamide / 16 h / Ambient temperature

4: 98 percent / trifluoroacetic acid / CH₂Cl₂ / 16 h / Ambient temperature

5: 100 percent / Et₃N / CH₂Cl₂ / 0.75 h / -70 °C

6: 95 percent / aq. NaOH / methanol / 3 h / 50 °C

7: 1.) CDI, 2.) NH₃ / 1.) THF, RT, 3 h, 2.) THF, EtOH, a.) RT, 16 h, b.) reflux, 4 h

With sodium hydroxide; ammonia; hydrogen; potassium carbonate; triethylamine; acetyl chloride; 1,1'-carbonyldiimidazole; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

Reference yield:

Ethyl 3-cyclopropyl-3-oxopropionate (24922-02-9) → saprisartan (146623-69-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 72 percent / aq. NaNO₂ / acetic acid / 4 h / Ambient temperature

2: 60 percent / H₂, AcCl / 5percent Pd/C / ethanol / 5 h / 760 Torr / Ambient temperature

3: 24 percent / Et₃N / ethanol

4: 62 percent / K₂CO₃ / dimethylformamide / 16 h / Ambient temperature

5: 98 percent / trifluoroacetic acid / CH₂Cl₂ / 16 h / Ambient temperature

6: 100 percent / Et₃N / CH₂Cl₂ / 0.75 h / -70 °C

7: 95 percent / aq. NaOH / methanol / 3 h / 50 °C

8: 1.) CDI, 2.) NH₃ / 1.) THF, RT, 3 h, 2.) THF, EtOH, a.) RT, 16 h, b.) reflux, 4 h

With sodium hydroxide; ammonia; hydrogen; potassium carbonate; triethylamine; acetyl chloride; 1,1'-carbonyldiimidazole; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

upstream raw materials:

1-<<3-bromo-2-<2-<<(trifluoromethyl)sulfonyl>amino>phenyl>-5-benzofuranyl>methyl>-4-cyclopropyl-2-ethyl-1H-imidazole-5-carboxylic acid

5-methylbenzofuran

2-bromobenzoic acid methyl ester

2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid

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