163137-45-9

Basic information

• Product Name: 2-Amino-5-chloro-pyridine-3-sulfonyl chloride
• Synonyms: 2-Amino-5-chloro-pyridine-3-sulfonyl chloride;2-amino-5-chloro-3-Pyridinesulfonyl chloride;2-Amino-5-chloro-pyridine-3-sulphonylchloride
• CAS NO: 163137-45-9
• Molecular Formula: C5H4Cl2N2O2S
• Molecular Weight: 227.06846
• Mol File: 163137-45-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Amino-5-chloro-pyridine-3-sulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-chloro-pyridine-3-sulfonyl chloride(163137-45-9)
• EPA Substance Registry System: 2-Amino-5-chloro-pyridine-3-sulfonyl chloride(163137-45-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 163137-45-9(Hazardous Substances Data)

Usage

Main properties

Derivative of pyridine
Contains a sulfonyl chloride functional group

Specific content

Key intermediate in the synthesis of pharmaceuticals and agrochemicals
Building block in the production of drugs such as antihypertensive agents and antithrombotic drugs
Used in the manufacture of dyes, pigments, and other specialty chemicals
Reactive and potentially hazardous chemical

Upstream product

• 1072-98-6 5-chloro-2-pyridylamine 

Downstream Products

• 1298029-96-5 [2-(4-methoxybenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid 
• 1298029-95-4 [2-(2,4,5-trifluorobenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid 
• 1298029-94-3 [2-(4-(trifluoromethyl)benzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid 
• 1298029-93-2 [2-(3-nitrobenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid 
• 1298029-92-1 [2-(4-bromo-2-fluorobenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid 
• 1298029-81-8 [2-(4-methoxybenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid methyl ester 
• 1298029-80-7 [2-(2,4,5-trifluorobenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid methyl ester 
• 1298029-79-4 [2-(4-(trifluoromethyl)benzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid methyl ester 
• 1298029-78-3 [2-(3-nitrobenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid methyl ester 
• 1298029-77-2 [2-(4-bromo-2-fluorobenzyl)-7-chloro-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxid-4-yl] acetic acid methyl ester 
• 163137-44-8 2-amino-5-chloropyridine-3-sulfonamide 

Relevant articles and documents

Oxidative reaction of 2-aminopyridine-3-sulfonyl chlorides with tertiary amines

2-Aminopyridine-3-sulfonyl chlorides undergo a reaction with tertiary amines in the presence of air to produce sulfonylethenamines. The 2-aminopyridine-3-sulfonyl chloride apparently plays a dual role in the process promoting the aerobic oxidation of the amine and electrophilically trapping the resulting enamine.

3-alkylamino-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxides structurally related to diazoxide and pinacidil as potassium channel openers acting on vascular smooth muscle cells: Design, synthesis, and pharmacological evaluation

A series of 3-alkylamino-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxides structurally related to diazoxide and pinacidil were synthesized and tested as possible K(ATP) channel openers on isolated pancreatic endocrine tissue as well as on isolated vascular, intestinal, and uterine smooth muscle. In contrast to previously described 3-alkylamino-4H-pyrido[4,3-e]-1,2,4- thiadiazine 1,1-dioxides, most of the new compounds were found to be poorly active on B-cells but exhibited clear vasorelaxant properties. 3-(3,3- Dimethyl-2-butylamino)-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxide (4d) and 7-chloro-3-(3,3-dimethyl-2-butylamino)-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxide (5d), two compounds bearing the alkyl side chain of pinacidil, were found to be the most active representatives of their respective series on rat aorta rings. 3-Cycloalkylalkylamino- and 3-aralkylamino-7-chloro-4H- pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxides also expressed myorelaxant activity on electrically stimulated guinea pig ileum and on oxytocin-induced contractions of the rat uterus. Further biological investigations (86Rb efflux measurements, vasodilator potency on 30 and 80 mM KCl-induced contractions in the absence and presence of glibenclamide) revealed that compounds 4d and 5d, but not compound 5f, expressed the pharmacological profile of classical K(ATP) channel openers. In conclusion, by changing the position of the nitrogen atom in the pyridine ring, we now have obtained a family of drugs expressing an opposite tissue selectivity. Taken as a whole, the present findings also suggest that 3-alkylamino-4H-pyrido[2,3-e]-1,2,4- thiadiazine 1,1-dioxides such as 4c, 4d, 5c, and 5d may be considered as new examples of K(ATP) channel openers expressing a pharmacological profile similar to that of pinacidil and diazoxide.