(3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

Base Information

• Chemical Name: (3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide
• CAS No.: 175340-20-2
• Molecular Formula: C10H12N2O2S
• Molecular Weight: 224.28
• UNII: IA262432Y9
• DSSTox Substance ID: DTXSID40938656
• Nikkaji Number: J1.978.206I
• Wikipedia: S-18986
• Wikidata: Q5552687
• ChEMBL ID: CHEMBL320642
• Mol file: 175340-20-2.mol

Synonyms:(S)-2,3-dihydro-(3,4)cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide;S 18986;S 18986-1;S-18986;S18986;S18986-1

Chemical Property of (3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

Chemical Property:

• PSA: 57.79000
• LogP: 2.37940
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 224.06194880
• Heavy Atom Count: 15
• Complexity: 349

Purity/Quality:

99%, ^*data from raw suppliers

S 18986 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2NS(=O)(=O)C3=CC=CC=C3N2C1
• Isomeric SMILES: C1C[C@@H]2NS(=O)(=O)C3=CC=CC=C3N2C1
• Recent ClinicalTrials: Efficacy and Safety of S18986 in the Treatment of Mild Cognitive Impairment Patients
• Recent EU Clinical Trials: Efficacy of 15 mg and 50 mg of S 18986 on cognitive symptoms in Mild Cognitive Impairment patients treated over a 12-month oral administration period.
• Uses: S 18986 is a novel cognitive enhancer.

Technology Process of (3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

There total 7 articles about (3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-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:

2,3-Dihydro-1H-pyrrolo<2,1-c><1,2,4>benzothiadiazin-5,5-dioxid (37121-62-3) → S18986 (175340-20-2)

Guidance literature:

With nitrogen; potassium tert-butylate; hydrogen; In isopropyl alcohol; toluene;

Reference yield:

5,5-dioxo-3,5-dihydro-2H-5λ6-benzo[e]pyrrolo[2,1-c][1,2,4]thiadiazin-1-one (4826-18-0) → 2,3,3a,4-tetrahydro-1H-benzo[e]pyrrolo[2,1-c][1,2,4]thiadiazine 5,5-dioxide (37121-70-3,175340-20-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 4 ℃;

Reference yield:

2,3-Dihydro-1H-pyrrolo<2,1-c><1,2,4>benzothiadiazin-5,5-dioxid (37121-62-3) → (R)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine-5,5-dioxide (175340-20-2) + S18986 (175340-20-2)

Guidance literature:

With lithium aluminium tetrahydride; (+)-(2S,4R)-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol; In diethyl ether; at 0 ℃; for 4h; Product distribution; other reagents, solvent, temperature;

DOI:10.1016/S0960-894X(96)00547-1

upstream raw materials:

2,3-Dihydro-1H-pyrrolo<2,1-c><1,2,4>benzothiadiazin-5,5-dioxid

5,5-dioxo-3,5-dihydro-2H-5λ⁶-benzo[e]pyrrolo[2,1-c][1,2,4]thiadiazin-1-one

2-AMINOBENZENESULFONAMIDE

Refernces

• 1、 Cobley, Christopher J.,Foucher, Elsa,Lecouve, Jean-Pierre,Lennon, Ian C.,Ramsden, James A.,Thominot, Gilles. "The synthesis of S 18986, a chiral AMPA receptor modulator, via catalytic asymmetric hydrogenation". . p. 3431 - 3433. Retrieved 2003.
• 2、 -. "Benzothiadiazine compound". . . Retrieved 2008/06/13.