methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate

Base Information

• Chemical Name: methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate
• CAS No.: 448906-42-1
• Molecular Formula: C₁₄H₁₀N₂O₃S
• Molecular Weight: 286.311
• Hs Code.: 2934100090
• European Community (EC) Number: 630-600-3
• DSSTox Substance ID: DTXSID70405386
• Nikkaji Number: J1.838.788C
• Wikidata: Q27164789
• ChEMBL ID: CHEMBL1324296
• Mol file: 448906-42-1.mol

Synonyms:448906-42-1;methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate;ITE;Methyl 2-(1H-indole-3-carbonyl)-1,3-thiazole-4-carboxylate;2-(1H-INDOL-3-YLCARBONYL)-4-THIAZOLECARBOXYLIC ACID METHYL ESTER;CHEMBL1324296;AHR agonist;ITE (cancer);D07IZS;The endogeneous AHR ligand;SCHEMBL422944;CHEBI:93059;DTXSID70405386;KDDXOGDIPZSCTM-UHFFFAOYSA-N;HMS3268G16;AMY29062;BCP17758;EX-A1251;ITE (cancer), AhR Pharmaceuticals;4-Thiazolecarboxylic acid, 2-(1H-indol-3-ylcarbonyl)-, methyl ester;BDBM50506039;MFCD06411597;AKOS016010400;CS-5141;SB17198;NCGC00159529-01;NCGC00159529-02;NCGC00159529-03;AS-55789;BI166811;HY-19317;FT-0732784;A22724;C75214;BRD-K60298136-001-01-7;Q27164789;2-(1'H-Indole-3'-carbonyl)-thiazole-4-carboxylic acid;2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylicacidMethylester;2-[1H-indol-3-yl(oxo)methyl]-4-thiazolecarboxylic acid methyl ester

Chemical Property of methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 6.24E-11mmHg at 25°C
• Refractive Index: 1.688
• Boiling Point: 520.4 °C at 760 mmHg
• PKA: 14.38±0.30(Predicted)
• Flash Point: 268.5 °C
• PSA: 100.29000
• Density: 1.427 g/cm³
• LogP: 2.64200
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 30 mg/mL, soluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 286.04121336
• Heavy Atom Count: 20
• Complexity: 404

Purity/Quality:

98%,99%, ^*data from raw suppliers

ITE ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CSC(=N1)C(=O)C2=CNC3=CC=CC=C32
• Uses: ITE is an endogenous AHR ligand that parenterally or orally induces FoxP3+ Treg that suppress exprimental autoimmune encephalomyelitis. ITE promotes the induction of active immunology tolerance and identifies nontoxic endogenous AHR ligands.

Technology Process of methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate

There total 15 articles about methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate 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: 88.0%

(4R)-2-(1'H-indole-3'-carbonyl)-4,5-dihydrothiazole-4-carboxylic acid methyl ester → ITE (448906-42-1)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 3h;

Reference yield: 84.59%

2-(1'H-indole-3'-carbonyl)-4,5-dihydrothiazole-4-carboxylic acid methyl ester → ITE (448906-42-1)

Guidance literature:

With manganese(IV) oxide; In tetrahydrofuran; for 4h; Reflux;

Reference yield: 66.0%

cysteine methyl ester hydrochloride (5714-80-7,18598-63-5,70361-61-4) + 1H-indol-3-yl(oxo)acetonitrile (19194-62-8) → ITE (448906-42-1)

Guidance literature:

cysteine methyl ester hydrochloride; 1H-indol-3-yl(oxo)acetonitrile; With pyridine; hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; at 40 ℃; for 2h;

With N-Bromosuccinimide; In dichloromethane; water; at 0 ℃; for 1h;

upstream raw materials:

indolyl-3-glyoxylyl chloride

(2R)-2-[2'-(1H-indol-3-yl)-2'-oxo-acetyloamino]-3-mercaptopropionic acid methyl ester

methyl 3-bromo-2-oxopropanoate

indole

Refernces

• 1、 -. "PROCESSES FOR THE PREPARATION OF ARYL HYDROCARBON RECEPTOR LIGANDS". . . Retrieved 2021/01/25.
• 2、 -. "EFFICIENT AND SCALABLE SYSTHESIS OF 2-(1'H-INDOLE-3'-CARBONYL)-THIAZOLE-4-CARBOXYLIC ACID METHYL ESTER AND ITS STRUCTURAL ANALOGS". . . Retrieved 2016/06/01.