4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide

Base Information

• Chemical Name: 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide
• CAS No.: 372497-52-4
• Molecular Formula: C₁₈H₁₀Br₂ClN₃OS
• Molecular Weight: 511.624
• European Community (EC) Number: 684-519-3
• UNII: 8R2YWY4LXF
• DSSTox Substance ID: DTXSID60359667
• Nikkaji Number: J3.560.884B
• Wikipedia: DS-1_(drug)
• Wikidata: Q5206094
• ChEMBL ID: CHEMBL4213357
• Mol file: 372497-52-4.mol

Synonyms:372497-52-4;DS1;4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide;CHEMBL4213357;4-Chloro-N-[6,8-dibromo-2-(2-thienyl)imidazo[1,2-a]pyridin-3-yl]benzamide;8R2YWY4LXF;D03IZV;4-chloro-N-(6,8-dibromo-2-thiophen-2-ylimidazo[1,2-a]pyridin-3-yl)benzamide;Oprea1_660341;DS-1 (DRUG);GTPL4183;DTXSID60359667;BDBM50457439;STK706326;4-Chloro-N-[6,8-dibromo-2-(2-thienyl)imidazo[1,2-a]pyridine-3-yl]benzamide;AKOS001667044;DS1, >=98% (HPLC);EU-0078283;J3.560.884B;EN300-18501257;SR-01000493101;Q5206094;SR-01000493101-1;4-chloro-N-(6,8-dibromo-2-thien-2-ylimidazo[1,2-a]pyridin-3-yl)benzamide;Benzamide, 4-chloro-N-[6,8-dibromo-2-(2-thienyl)imidazo[1,2-a]pyridin-3-yl]-

Chemical Property of 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide

Chemical Property:

• PSA: 78.13000
• LogP: 6.87750
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 510.85794
• Heavy Atom Count: 26
• Complexity: 523

Purity/Quality:

97% ^*data from raw suppliers

DS1 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=C(N3C=C(C=C(C3=N2)Br)Br)NC(=O)C4=CC=C(C=C4)Cl
• Uses: DS1 is a GABAA receptor agonist which can stimulate gonadotropin subunit gene expression in mouse.

Technology Process of 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide

There total 5 articles about 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide 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: 59.0%

6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine + 4-chloro-benzoyl chloride (122-01-0) → 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide (372497-52-4)

Guidance literature:

With pyridine; In toluene; at 25 ℃; for 1h;

DOI:10.1021/acs.jmedchem.7b01484

Reference yield:

2-amino-3,5-dibromopyridine (35486-42-1) → 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide (372497-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium metabisulfite / water / 0.5 h / 25 °C

1.2: 2 h / 100 °C

2.1: water; ethanol / 5 h / 25 - 100 °C

3.1: pyridine / toluene / 1 h / 25 °C

With pyridine; sodium metabisulfite; In ethanol; water; toluene;

DOI:10.1021/acs.jmedchem.7b01484

Reference yield:

thiophene-2-carbaldehyde (98-03-3) → 4-chloro-N-[6,8-dibromo-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl]benzamide (372497-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium metabisulfite / water / 0.5 h / 25 °C

1.2: 2 h / 100 °C

2.1: water; ethanol / 5 h / 25 - 100 °C

3.1: pyridine / toluene / 1 h / 25 °C

With pyridine; sodium metabisulfite; In ethanol; water; toluene;

DOI:10.1021/acs.jmedchem.7b01484

upstream raw materials:

4-chloro-benzoyl chloride

thiophene-2-carbaldehyde

2-amino-3,5-dibromopyridine