7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide

Base Information

• Chemical Name: 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide
• CAS No.: 22503-72-6
• Molecular Formula: C8H9 Cl N2 O2 S
• Molecular Weight: 232.691
• Hs Code.: 2933990090
• European Community (EC) Number: 839-213-6
• UNII: 689UW7PT68
• DSSTox Substance ID: DTXSID70936887
• Nikkaji Number: J678.590E
• Wikipedia: IDRA-21
• Wikidata: Q5970086
• ChEMBL ID: CHEMBL77862
• Mol file: 22503-72-6.mol

Synonyms:7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-S,S-dioxide;IDRA 21;IDRA-21

Chemical Property of 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide

Chemical Property:

• Vapor Pressure: 8.98E-07mmHg at 25°C
• Melting Point: 209 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 405.1°Cat760mmHg
• PKA: 9.78±0.40(Predicted)
• Flash Point: 198.8°C
• PSA: 66.58000
• Density: 1.394g/cm³
• LogP: 2.93740
• Storage Temp.: Store at RT
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 232.0073264
• Heavy Atom Count: 14
• Complexity: 314

Purity/Quality:

99.89% ^*data from raw suppliers

IDRA 21 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1NC2=C(C=C(C=C2)Cl)S(=O)(=O)N1
• Uses: IDRA-21 inhibits AMPA receptor desensitization and enhances cognition by a related mechanism. IDRA-21 is more able to cross the blood-brain barrier than Cyclothiazide (C988960). IDRA-21 is a benzothiadiazine derivative and a positive allosteric modulator of glutamate AMPA receptors (1,2,3,4). It is able to increase excitatory synaptic strength by inhibiting AMPA receptor desensitization. IDRA 21 may exhibit therapeutic effects to ameliorate memory deficits in patients with cognitive impairments such as Alzheimer''s disease.

Technology Process of 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide

There total 5 articles about 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide 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: 80.0%

2-amino-5-chlorobenzenesulfonamide (5790-69-2) + ethanol (64-17-5) → IDRA 21 (22503-72-6,163936-78-5)

Guidance literature:

With tert.-butylhydroperoxide; at 110 ℃; for 12h;

DOI:10.1016/j.tetlet.2018.04.054

Reference yield:

2-amino-5-chlorobenzenesulfonamide (5790-69-2) + acetaldehyde (75-07-0,9002-91-9) → IDRA 21 (22503-72-6,163936-78-5)

Guidance literature:

In acetonitrile;

DOI:10.1021/jm00338a008

Reference yield:

4-Chlor-2-acetylsulfamoyl-acetanilid (90794-87-9) → IDRA 21 (22503-72-6,163936-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH

2: acetonitrile

With sodium hydroxide; In acetonitrile;

DOI:10.1021/jm00338a008

upstream raw materials:

2-amino-5-chlorobenzenesulfonamide

acetaldehyde

4-Chlor-2-acetylsulfamoyl-acetanilid

2-acetylamino-benzenesulfonic acid acetylamide

Downstream raw materials:

2-amino-5-chloro-N-ethylbenzenesulfonamide

5-chloro-2-(ethylamino)benzenesulfonamide

N-acetyl-5-chloro-2-nitrobenzenesulfonamide

Refernces

• 1、 Larsen, Anja Probst,Francotte, Pierre,Frydenvang, Karla,Tapken, Daniel,Goffin, Eric,Fraikin, Pierre,Caignard, Daniel-Henri,Lestage, Pierre,Danober, Laurence,Pirotte, Bernard,Kastrup, Jette Sandholm. "Synthesis and Pharmacology of Mono-, Di-, and Trialkyl-Substituted 7-Chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides Combined with X-ray Structure Analysis to Understand the Unexpected Structure-Activity Relationship at AMPA Receptors". . p. 378 - 390. Retrieved 2016/04/05.