(S)-5-Bromo-N-((1-ethylpyrrolidin-2-YL)methyl)-2,3-dimethoxybenzamide

Base Information

• Chemical Name: (S)-5-Bromo-N-((1-ethylpyrrolidin-2-YL)methyl)-2,3-dimethoxybenzamide
• CAS No.: 107188-66-9
• Molecular Formula: C₁₆H₂₃BrN₂O₃
• Molecular Weight: 371.274
• UNII: GH32HX9WCX
• DSSTox Substance ID: DTXSID40432689
• Nikkaji Number: J338.979K
• Wikidata: Q82246796
• Pharos Ligand ID: TT87GA1S2MW7
• ChEMBL ID: CHEMBL289330
• Mol file: 107188-66-9.mol

Synonyms:5-bromo-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,3-dimethoxybenzamide;cyclopropyl-FLB 457;FLB 457;FLB 457, (R)-isomer;FLB 457, (S)-isomer;FLB 457, hydrobromide, (R)-isomer;FLB 457, hydrobromide, (S)-isomer;FLB-457

Chemical Property of (S)-5-Bromo-N-((1-ethylpyrrolidin-2-YL)methyl)-2,3-dimethoxybenzamide

Chemical Property:

• Vapor Pressure: 3.1E-07mmHg at 25°C
• Boiling Point: 419.2°Cat760mmHg
• Flash Point: 207.3°C
• PSA: 54.29000
• Density: 1.292g/cm³
• LogP: 3.19310
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 370.08921
• Heavy Atom Count: 22
• Complexity: 369

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C(=CC(=C2)Br)OC)OC
• Isomeric SMILES: CCN1CCC[C@H]1CNC(=O)C2=C(C(=CC(=C2)Br)OC)OC

Technology Process of (S)-5-Bromo-N-((1-ethylpyrrolidin-2-YL)methyl)-2,3-dimethoxybenzamide

There total 8 articles about (S)-5-Bromo-N-((1-ethylpyrrolidin-2-YL)methyl)-2,3-dimethoxybenzamide 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: 100.0%

5-bromo-2,3-dimethoxybenzoic acid chloride (107188-91-0) + (R)-2-aminomethyl-1-ethylpyrrolidine (22795-97-7) → (+)-(R)-5-bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dimethoxybenzamide (107188-75-0,107188-66-9)

Guidance literature:

In dichloromethane; Ambient temperature;

DOI:10.1021/jm00170a040

Reference yield: 87.5%

5-bromo-2,3-dimethoxybenzoic acid (72517-23-8) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) → [3H]-FLB 457 (107188-74-9,107188-66-9)

Guidance literature:

5-bromo-2,3-dimethoxybenzoic acid; With thionyl chloride; In toluene; at 60 ℃; for 1h; Inert atmosphere;

(S)-2-(Aminomethyl)-1-ethylpyrrolidine; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere; Cooling with ice;

Reference yield: 78.0%

5-bromo-2,3-dimethoxybenzoic acid chloride (107188-91-0) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) → [3H]-FLB 457 (107188-74-9,107188-66-9)

Guidance literature:

In dichloromethane; for 4h; Ambient temperature;

DOI:10.1080/00397919108019800

upstream raw materials:

5-bromo-2,3-dimethoxybenzoic acid chloride

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

5-bromo-2,3-dimethoxybenzaldehyde

5-bromo-3-methoxysalicylaldehyde

Downstream raw materials:

(-)-(S)-N-<(1-Ethylpyrrolidin-2-yl)methyl>-2,3-dimethoxy-5-(trimethylsilyl)benzamide

epidepride

(-)-(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dimethoxybenzamide

Refernces

• 1、 -. "Pyrrolidine compounds, salts thereof, applications of compounds or salts thereof in nuclear magnetic probes and medicines, reagent, and medicine". Paragraph 0242; 0243; 0244. . Retrieved 2017/08/27.
• 2、 De Paulis,Smith. "Facile preparation of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dimethoxy-5- (tributyltin)benzamide from isoremoxipiride: The precursor of [125I]- and [123I]epidepride". . p. 1091 - 1095. Retrieved 2007/10/02.