Icopezil

Base Information

• Chemical Name: Icopezil
• CAS No.: 145508-78-7
• Molecular Formula: C23H25 N3 O2
• Molecular Weight: 375.47
• UNII: ERZ60E6B7C
• DSSTox Substance ID: DTXSID70932622
• Nikkaji Number: J684.157K
• Wikidata: Q27277324
• NCI Thesaurus Code: C99558
• Pharos Ligand ID: 3N8YKH3MQH2G
• ChEMBL ID: CHEMBL359570
• Mol file: 145508-78-7.mol

Synonyms:Icopezil;Icopezil [INN];145508-78-7;CP 118954;UNII-ERZ60E6B7C;ERZ60E6B7C;CID 5490675;CP-118954;CHEMBL359570;CP 118,954;CHEMBL329012;3-[2-(1-benzylpiperidin-4-yl)ethyl]-5,7-dihydropyrrolo[3,2-f][1,2]benzoxazol-6-one;D0B2BQ;ICOPEZIL [WHO-DD];SCHEMBL194482;DTXSID70932622;BDBM50032162;Q27277324;3-[2-(1-Benzylpiperidin-4-yl)ethyl]-2,5-dihydro-6H-[1,2]oxazolo[4,5-f]indol-6-one;3-(2-(1-BENZYL-4-PIPERIDYL)ETHYL)-5,7-DIHYDRO-6H-PYRROLO(3,2-F)-1,2-BENZISOXAZOL-6-ONE;3-[2-(1-Benzyl-piperidin-4-yl)-ethyl]-5,7-dihydro-isoxazolo[4,5-f]indol-6-one;compound with (Z)-but-2-enedioic acid

Chemical Property of Icopezil

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 581.4°Cat760mmHg
• Flash Point: 305.4°C
• PSA: 61.86000
• Density: 1.227g/cm³
• LogP: 4.19020
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 375.19467705
• Heavy Atom Count: 28
• Complexity: 542

Purity/Quality:

99% ^*data from raw suppliers

ICOPEZIL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1CCC2=NOC3=C2C=C4CC(=O)NC4=C3)CC5=CC=CC=C5
• Uses: [icopezil] Alzheimer’s disease treatment (cognition enhancer); cognition adjuvant; inhibitor (acetylcholinesterase).

Technology Process of Icopezil

There total 7 articles about Icopezil 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:

5,7-dihydro-3-methyl-6H-pyrrolo<3,2-f>-1,2-benzisoxazol-6-one (145509-11-1) → icopezil (145508-78-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 °C

2: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

3: Na₂CO₃ / dimethylformamide / 4 h / Ambient temperature

With sodium carbonate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00015a002

Reference yield:

5-acetyl-1,3-dihydro-6-hydroxy-2H-indol-2-one, 5-oxime → icopezil (145508-78-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 54 percent / 2 h / 80 °C

2: 65 percent / pyridine / dimethylformamide / 4 h / 125 - 130 °C

3: 76 percent / LDA / tetrahydrofuran / 4 h / -78 °C

4: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

5: Na₂CO₃ / dimethylformamide / 4 h / Ambient temperature

With pyridine; sodium carbonate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00015a002

Reference yield:

5-acetyl-1,3-dihydro-6-hydroxy-2H-indol-2-one, 5-oxime acetate (166756-71-4) → icopezil (145508-78-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / pyridine / dimethylformamide / 4 h / 125 - 130 °C

2: 76 percent / LDA / tetrahydrofuran / 4 h / -78 °C

3: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

4: Na₂CO₃ / dimethylformamide / 4 h / Ambient temperature

With pyridine; sodium carbonate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00015a002

upstream raw materials:

benzyl bromide

CP-144,885

5,7-dihydro-3-methyl-6H-pyrrolo<3,2-f>-1,2-benzisoxazol-6-one

5-acetyl-1,3-dihydro-6-hydroxy-2H-indol-2-one, 5-oxime acetate

Refernces

• 1、 -. "Processes and intermediates for preparing 5, 7-dihydro-3-?2-(1-benzylpiperidin-4-yl)ethyl-!6H-pyrrolo-?4, 5-F!-1, 2-benzisoxazol-6-one". . . Retrieved 2008/06/13.
• 2、 Villalobos,Butler,Chapin,Chen,DeMattos,Ives,Jones,Liston,Nagel,Nason,Nielsen,Ramirez,Shalaby,White. "5,7-Dihydro-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-6H-pyrrolo[3,2- f]1,2-benzisoxazol-6-one: A potent and centrally-selective inhibitor of acetylcholinesterase with an improved margin of safety". . p. 2802 - 2808. Retrieved 2007/10/02.