141761-83-3

Basic information

• Product Name: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester
• Synonyms: 6-Chloro-3,4-Dihydro-4-Methyl-3-Oxo-2H-1,4-Benzoxazine-8-CarboxylicAcidMethlyEster;6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester;2H-1,4-Benzoxazine-8-carboxylicacid,6-chloro-3,4-dihydro-4-Methyl-3-oxo-, Methyl ester;Methyl 6-chloro-4-Methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate;methyl 6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxylate;2H-1,4-Benzoxazine-8-carboxylic
• CAS NO: 141761-83-3
• Molecular Formula: C₁₁H₁₀ClNO₄
• Molecular Weight: 255.65
• EINECS: 1533716-785-6
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 141761-83-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 498.8 °C at 760 mmHg
• Flash Point: 255.5 °C
• Appearance: /
• Density: 1.384
• Vapor Pressure: 4.4E-10mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: 2-8°C
• PKA: -1.00±0.20(Predicted)
• CAS DataBase Reference: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester(141761-83-3)
• EPA Substance Registry System: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester(141761-83-3)

Safety Data

• Hazardous Substances Data: 141761-83-3(Hazardous Substances Data)

Usage

Uses

Azasetron intermediate.

InChI:InChI=1/C11H10ClNO4/c1-13-8-4-6(12)3-7(11(15)16-2)10(8)17-5-9(13)14/h3-4H,5H2,1-2H3

Upstream product

• 5043-81-2 3-amino-5-chloro-2-hydroxybenzoic acid methyl ester 
• 79-04-9 chloroacetyl chloride 
• 616-38-6 carbonic acid dimethyl ester 
• 4068-78-4 methyl 5-chloro-2-hydroxybenzoate 
• 123040-75-5 methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate 
• 74-88-4 methyl iodide 
• 5043-79-8 5-chloro-2-hydroxy-3-nitrobenzoic acid methyl ester 

Downstream Products

• 123040-16-4 Azasetron hydrochloride 
• 141762-06-3 6-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-benzyl-piperidin-4-yl)-amide 
• 141762-05-2 6-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-benzyl-piperidin-3-yl)-amide 
• 123040-69-7 azasetron 
• 123040-50-6 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride 
• 123040-79-9 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid 

Relevant articles and documents

Novel preparation method of azasetron hydrochloride

The invention provides a novel preparation method of azasetron hydrochloride, belonging to the technical field of medicine synthesis. According to the method, methyl 5-chlorosalicylate is used as a raw material; after acetic anhydride nitrification and stannous chloride reduction at room temperature, dimethyl carbonate is used as a methylation reagent, and an intermediate V (6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester) is synthesized by adopting a one-pot method; the intermediate V is hydrolyzed to obtain 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-formic acid (VI); and the compound reacts with free 3-aminoquinuclidine dihydrochloride for 1 h under the catalysis of TBTU to form a salt so as to obtain I (azasetron hydrochloride). According to the method, the yield of each step is high; aftertreatment is simple; the reaction time of each step is short; conditions are mild; low-toxicity environment-friendly reagents are adopted; energy consumption is reduced; cost is saved; and industrial production is better facilitated.

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

A series of 3,4-dihydro-3-oxo-1,4-benzoxazine-8-carboxamide derivatives was synthesized and evaluated for serotonin-3 (5-HT3) receptor antagonistic activity assessed by their ability to antagonize the von Bezold-Jarish (BJ) effect in rats. Derivatives bearing 1-azabicyclo[2.2.2]oct-3-yl moiety as a basic function attached to the carboxamide at position 8 showed more potent antagonistic activity than those bearing the other three basic moieties. Structure activity relationships of this series showed that methyl and chloro groups were more effective as substituents at positions 4 and 6, respectively. The representative compound 15 (Y-25130) in this series showed potent antagonistic activity on the BJ effect (ED50 = 1.3 μg/kg i.v.), high affinity for 5-HT3 receptor (K(i) = 2.9 nM) and complete protection against cisplatin-induced emesis in dogs at a dose of 0.1 mg/kg i.v.