Azasetron

Base Information

• Chemical Name: Azasetron
• CAS No.: 123040-69-7
• Deprecated CAS: 123039-99-6,197068-87-4
• Molecular Formula: C₁₇H₂₀ClN₃O₃
• Molecular Weight: 349.817
• UNII: 77HC7URR9Z
• DSSTox Substance ID: DTXSID7045651
• Nikkaji Number: J391.611A
• Wikipedia: Azasetron
• Wikidata: Q4832285
• NCI Thesaurus Code: C73101
• Pharos Ligand ID: UVRWSXY3QQ6Z
• ChEMBL ID: CHEMBL1598608
• Mol file: 123040-69-7.mol

Synonyms:azasetron;azasetron, (+-)-isomer;N-(1-azabicyclo(2.2.2)oct-3-yl)-6-chloro-4-methyl-3-oxo-3,4 -dihydro-2H-1,4-benzoxazine-8-carboxamide hydrochloride;Y 25130;Y-25130

Chemical Property of Azasetron

Chemical Property:

• Appearance/Colour: white crystalline
• Vapor Pressure: 1.75E-12mmHg at 25°C
• Melting Point: 301-303 °C
• Boiling Point: 558 °C at 760 mmHg
• PKA: 13.31±0.20(Predicted)
• Flash Point: 291.2 °C
• PSA: 61.88000
• Density: 1.42 g/cm³
• LogP: 1.91300
• Storage Temp.: -20°C Freezer
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 349.1193192
• Heavy Atom Count: 24
• Complexity: 523

Purity/Quality:

99% ^*data from raw suppliers

Azasetron ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)COC2=C(C=C(C=C21)Cl)C(=O)NC3CN4CCC3CC4
• Recent NIPH Clinical Trials: A Phase II study of Aprepitant in patients receiving chemotherapy included carboplatin for gynecological canncer.
• Uses: As a 5-HT3 receptor antagonist, Azasetron hydrochloride can be used as an antiemetic.
• Therapeutic Function: Antiemetic

Technology Process of Azasetron

There total 10 articles about Azasetron 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: 86.3%

3-aminoquinuclidine dihydrochloride (6530-09-2) + 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid (123040-79-9) → azasetron (123040-69-7,123040-93-7,123040-95-9,123039-99-6)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; at 0 - 10 ℃;

Reference yield:

6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester (141761-83-3) → azasetron (123040-69-7,123040-93-7,123040-95-9,123039-99-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating

2: SOCl₂, DMF / 1,2-dichloro-ethane / 2 h / 60 °C

3: CHCl₃ / 1 h / Ambient temperature

With sodium hydroxide; thionyl chloride; N,N-dimethyl-formamide; In ethanol; chloroform; 1,2-dichloro-ethane;

DOI:10.1248/cpb.40.624

Reference yield:

methyl 5-chloro-2-hydroxybenzoate (4068-78-4) → azasetron (123040-69-7,123040-93-7,123040-95-9,123039-99-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / HNO₃, conc. H₂SO₄ / 1 h / 0 - 5 °C

2: 79 percent / 0.78N aq. NH₄Cl, Fe / toluene / 1 h / 85 - 90 °C

3: aq. NaHCO₃ / CHCl₃ / 2 h / 0 - 10 °C

4: K₂CO₃ / dimethylformamide / 2 h / 70 °C

5: 82.2 percent / K₂CO₃ / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h

6: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating

7: SOCl₂, DMF / 1,2-dichloro-ethane / 2 h / 60 °C

8: CHCl₃ / 1 h / Ambient temperature

With sodium hydroxide; thionyl chloride; sulfuric acid; nitric acid; iron; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; N,N-dimethyl-formamide; In ethanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.40.624

upstream raw materials:

quinuclidin-3-amine

6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride

methyl 5-chloro-2-hydroxybenzoate

3-amino-5-chloro-2-hydroxybenzoic acid methyl ester

Downstream raw materials:

Azasetron hydrochloride

Refernces

• 1、 -. "A method for synthesizing arab League grips Si Qiong hydrochloric acid". . . Retrieved 2017/02/09.
• 2、 Kawakita,Kuroita,Yasumoto,Sano,Inaba,Fukuda,Tahara. "Synthesis and pharmacology of 3,4-dihydro-3-oxo-1,4-benzoxazine-8-carboxamide derivatives, a new class of potent serotonin-3 (5-HT3) receptor antagonists". . p. 624 - 630. Retrieved 2007/10/02.