2-(4-Acetamido-3-((4-chlorophenyl)thio)-2-methyl-1H-indol-1-yl)acetic acid

Base Information

• Chemical Name: 2-(4-Acetamido-3-((4-chlorophenyl)thio)-2-methyl-1H-indol-1-yl)acetic acid
• CAS No.: 802904-66-1
• Deprecated CAS: 1263765-94-1
• Molecular Formula: C₁₉H₁₇ClN₂O₃S
• Molecular Weight: 388.875
• UNII: 2AD53WQ2CX
• ChEMBL ID: CHEMBL1914489
• DSSTox Substance ID: DTXSID901025620
• Metabolomics Workbench ID: 153020
• Pharos Ligand ID: JT69D9FHHVMK
• Wikidata: Q27074719
• Mol file: 802904-66-1.mol

Synonyms:AZD1981

Chemical Property of 2-(4-Acetamido-3-((4-chlorophenyl)thio)-2-methyl-1H-indol-1-yl)acetic acid

Chemical Property:

• Boiling Point: 676.8±55.0 °C(Predicted)
• PKA: 4.06±0.10(Predicted)
• PSA: 100.12000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 5.44680
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥19.8 mg/mL in DMSO
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 388.0648413
• Heavy Atom Count: 26
• Complexity: 527

Purity/Quality:

99%+, ^*data from raw suppliers

AZD1981 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C=CC=C2N1CC(=O)O)NC(=O)C)SC3=CC=C(C=C3)Cl
• Recent ClinicalTrials: Efficacy and Safety of Chemoattractant Receptor-homologous Molecule Expressed on T Helper Type 2 (CRTh2) Antagonist AZD1981 in Chronic Idiopathic Urticaria (CIU) Antihistamines
• Recent EU Clinical Trials: A double-blind, placebo-controlled, randomised, parallel-group, phase-II, multi-centre study to assess the efficacy, safety and tolerability of 4 twice daily doses and 2 once daily doses of AZD1981 given as tablets during 12 weeks in asthmatic patients treated with inhaled corticosteroids and long-acting-β2-agonists.
• Uses: AZD 1981 is an orally available selective DP2 antagonist in the treatment of asthma.

Technology Process of 2-(4-Acetamido-3-((4-chlorophenyl)thio)-2-methyl-1H-indol-1-yl)acetic acid

There total 15 articles about 2-(4-Acetamido-3-((4-chlorophenyl)thio)-2-methyl-1H-indol-1-yl)acetic acid 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: 97.0%

(4-acetylamino-2-methyl-1H-indol-1-yl)acetic acid (959619-21-7) → AZD-1981 (802904-66-1)

Guidance literature:

4,4'-dichlorodiphenyl disulfide; With trichloroisocyanuric acid; In ethyl acetate; at 20 ℃; for 0.25h;

(4-acetylamino-2-methyl-1H-indol-1-yl)acetic acid; In ethyl acetate; at 20 ℃; for 1.25h; Product distribution / selectivity;

Reference yield: 94.0%

ethyl [4-acetylamino-3-(4-chlorophenylsulfanyl)-2-methyl-1H-indol-1-yl]acetate (646515-19-7) → AZD-1981 (802904-66-1)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 59 - 65 ℃; for 0.5h; Inert atmosphere;

Reference yield:

4,4'-dichlorodiphenyl disulfide (1142-19-4) + ethyl [4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate (1260673-33-3) + acetic anhydride (108-24-7) → AZD-1981 (802904-66-1)

Guidance literature:

ethyl [4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; In xylene; for 2h; Inert atmosphere; Reflux;

4,4'-dichlorodiphenyl disulfide; With trichloroisocyanuric acid; In ethyl acetate; at 20 ℃; for 1.16667h; Inert atmosphere;

With water; sodium hydroxide; In ethanol; at 20 ℃; for 2h; Inert atmosphere;

upstream raw materials:

ethyl [4-acetylamino-3-(4-chlorophenylsulfanyl)-2-methyl-1H-indol-1-yl]acetate

(4-acetylamino-2-methyl-1H-indol-1-yl)acetic acid

4,4'-dichlorodiphenyl disulfide

ethyl [4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate

Refernces

• 1、 -. "INTERMEDIATES AND PROCESSES FOR THE PREPARATION OF 4- (ACETYLAMINO) ) -3- [ (4-CHLORO-PHENYL) THIO] -2-METHYL-1H-INDOLE-1-ACETIC ACID". Page/Page column 34. . Retrieved 2011/02/24.
• 2、 -. "NOVEL PROCESS". Page/Page column 8. . Retrieved 2008/06/13.