Category: 6684-39-5

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of aryl sulfonyl fluorides from aryl sulfonyl chlorides using sulfuryl fluoride (SO2F2) as fluoride provider, published in , which mentions a compound: 6684-39-5, Name is 2-Chloro-5-pyridinesulfonyl chloride, Molecular C5H3Cl2NO2S, Quality Control of 2-Chloro-5-pyridinesulfonyl chloride.

A highly efficient method for the synthesis of aryl sulfonyl fluorides ArSO2F [Ar = 4-MeC6H4, 4-PhC6H4, 4-ClC6H4, etc.] was developed from aryl sulfonyl chlorides using SO2F2 as fluoride source in up to 98% isolated yield under mild conditions. Gram scale experiments were also conducted, revealing the good practicality of this new protocol.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《2-Aminopyridine-5-sulfonamide and some derivatives》. Authors are Naegeli, C.; Kundig, W.; Brandenburger, H..The article about the compound:2-Chloro-5-pyridinesulfonyl chloridecas:6684-39-5,SMILESS:ClC1=NC=C(C=C1)[S](=O)(=O)Cl).Formula: C5H3Cl2NO2S. Through the article, more information about this compound (cas:6684-39-5) is conveyed.

The pyridine analog, 2-aminopyridine-5-sulfonamide (I), of the chemotherapeutically significant H2NC6H4SO2NH2, and a series of its derivatives substituted at the N atom of the side chain have been prepared from 2-chloropyridine-5-sulfonyl chloride (II) obtained either from 2-aminopyridine-5-sulfonic acid (III) or from N-methyl-2-pyridone-5-sulfonic acid (IV). A solution of 250 g. of 2-aminopyridine in 750 g. of H2SO4.H2O was heated at 200-10° for 5 hrs. with 0.5 g. Al powder and the cooled product was poured on ice. The washed precipitate was combined with further fractions from the mother liquor and crystallized from hot H2O, yielding 278 g. (60%) of III; Ac derivative, C7H8N2O4S, m. 300-2° (decomposition), from the Na salt which was converted to the difficultly soluble Cu salt. A suspension of 85 g. of finely powd. III in 600 cc. of 20% HCl at 10° was stirred with 50 g. (1.5 mols.) of NaNO2 in 125 cc. H2O. After 3 hrs. the solution was evaporated to dryness in vacuo, taken up in hot H2O and precipitated with alc., producing 83 g. (97%) of 2-pyridone-5-sulfonic acid (V), converted by chlorination with PCl5 (C. A. 25, 4267) into II. IV (2 g.), obtained by treating N-methyl-2-pyridone with Me2SO4 (Ger. 597,452, C. A. 28, 5083.5), was ground with 4.5 g. PCl5 and refluxed at 130-5° for 5 hrs. with a few drops of POCl3. The cold product was poured over ice and the solid mass was ground with NaHCO3, washed and dried. Extraction with petroleum ether gave 1.7 g. (82%) of II, m. 51°. Gradual addition of 50 g. II in 50 cc. Me2CO to well-stirred cold 20% NH4OH, evaporation and recrystallization from H2O produced 42.7 g. (94%) of iridescent crystals of 2-chloropyridine-5-sulfonamide (VI), C5H5ClN2O2S, m. 158-9°, converted by heating in a bomb-tube for 5 hrs. at 125-60° with 20% NH4OH into 2-aminopyridine-5-sulfonamide (VII), C5H7N3O2S, m. 175.0-6.5°; di-Bz derivative, C19H15N3O4S, m. 221-3°. By heating with the requisite amine under a reflux or, when necessary, in a bomb-tube, VI was converted into 2-ethylamino-, 2-diethylamino-, 2-butylamino-, 2-allylamino-, 2-benzylamino- and 2-phenylaminopyridine-5-sulfonamide, m. 190-1°, 116-17, 121-2°, 195-201°, 199-201° and 181-3°, resp. Heating 5 g. VI with 8 mols. of 33% EtNH2 in a bomb-tube at 135-50° for 4 hrs. yielded 2-ethylaminopyridine-5-sulfonethylamide, C9H15N3O2S, m. 139-41°. Cautious addition of 2.9 g. (2.2 mols.) of PhNH2 to 3 g. VI in 2.5 cc. benzene with cooling, washing the pasty residue with dilute HCl and recrystallization from alc. gave 3 g. (79%) of 2-chloropyridine-5-sulfonanilide, C11H9ClN2O2S, m. 149-51°, converted by heating in a bomb-tube for 2 hrs. at 100-30° with 20% NH4OH to 2-aminopyridine-5-sulfonanilide, m. 176-8°. The addition of 10 g. II in 10 g. anhydrous pyridine to 8.2 g. sulfanilamide in 15 g. pyridine below 40° precipitation with H2O and crystallization from dilute alc. gave 13 g. (79%) of N4-(2′-chloropyridine-5′-sulfonyl)sulfanilamide, C11H10ClN3O4S2, m. 200-2°, transformed by heating with 25% NH4OH in a bomb-tube for 8 hrs. at 130-50° into the corresponding 2′-amino compound, m. 200-2°. Addition of 3.7 g. VII in 6 cc. pyridine to 4 g. II in 4 g. pyridine below 35°, washing the precipitate from H2O with dilute HCl and drying in vacuo yielded 6.5 g. (99%) of orange crystalline 2-(2′-chloropyridine-5′-sulfonyl)aminopyridine-5-sulfonamide, C10H9ClN4O4S2, m. 253-5°, converted by autoclaving in saturated NH4OH for 5 hrs. at 7 atm. at 120-60° into the corresponding 2′-amino derivative, m. 260°. Heating a mixture of 5.5 g. VI and 5 g. morpholine (VIII) in a bomb-tube for 4 hrs. at 120° and crystallization of the product from H2O yielded 5.3 g. (76%) of 2-(N-morpholyl)pyridine-5-sulfonamide, C9H13N3O3S, m. 182-3°. The dropwise addition of 1.5 g. II in 5 cc. Me2CO to a well-stirred solution of 1.23 g. (2 mols.) VIII in 3 cc. H2O gave 1.7 g. (95%) of colorless platelets of 2-chloropyridine-5-sulfonmorpholide, C9H11ClN2O3S, m. 143-4°, converted by refluxing for 5 hrs. with 2 mols. VIII in xylene and recrystallizing the product from alc., in 85% yield, into colorless 2-(N-morpholyl)pyridine-5-sulfonmorpholide. C13H19N3O4S, m. 189-91°. All the above compounds are well tolerated and their action on mice infected with streptococci will be reported elsewhere. The extreme reduction of activity by substitution of the benzene ring in sulfanilamide type compounds “”by heterocyclic rings”” was reported by Tullar at the Dallas meeting of the Am. Chem. Soc. (1938).

When you point to this article, it is believed that you are also very interested in this compound(6684-39-5)Formula: C5H3Cl2NO2S and due to space limitations, I can only present the most important information.

Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Pan, Ting; Ding, Yanchao; Wu, Liyang; Liang, Liting; He, Xin; Li, Qianwen; Bai, Chuan; Zhang, Hui researched the compound: 2-Chloro-5-pyridinesulfonyl chloride( cas:6684-39-5 ).Computed Properties of C5H3Cl2NO2S.They published the article 《Design and synthesis of aminothiazole based Hepatitis B Virus (HBV) capsid inhibitors》 about this compound( cas:6684-39-5 ) in European Journal of Medicinal Chemistry. Keywords: antiviral HBV capsid protein inhibitor aminothiazole preparation structure activity. We’ll tell you more about this compound (cas:6684-39-5).

The capsid assembly is an essential step for Hepatitis B Virus (HBV) life cycle and is an important target for anti-HBV drug development. In this report, we identified a hit compound with aminothiazole structure by the high throughput screening (HTS) which inhibited the interaction of HBV capsid protein within the cells. The structure hopping and SAR studies of the hit compound afforded compound 79 with potent anti-HBV replication activity and good basic drug-like properties. The working mechanism studies showed that compound 79 could bind to the similar binding site of known HBV capsid inhibitor with heteroaryldihydropyrimidine (HAP) scaffold, through similar hydrophobic interactions but with a different hydrogen bond. This compound exerted potent inhibitory effect upon HBV production, either in cell culture or in mice with no obvious acute toxicity. We propose that further development of this compound could lead to novel potent anti-HBV inhibitors that target HBV capsid assembly.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Synthesis and antimicrobial activity of new 3,5-diarylidene-4-piperidone derivatives, published in 2016, which mentions a compound: 6684-39-5, mainly applied to diarylidene piperidone preparation antibacterial antifungal, SDS of cas: 6684-39-5.

Three series of heteroaromatic analogs diarylidene-4-piperidones I [Ar = C6H5, 4-FC6H4, 2-thienyl, etc.], [diarylidene(substituted)sulfonyl]piperidin-4-ones II [R1 = 3,5-Cl2-2-OHC6H2, 4-Cl-3-pyridyl, 3,5-Me2-4-isoxazolyl, etc.] and N-alkylcarbonyl-diarylidene-4-piperidones derivatives e.g., III, were synthesized. All the synthesized compounds were evaluated for their antimicrobial activity against six microbial strains, among them II [R1 = 3,5-Cl2-2-OHC6H2] showed best antifungal activity against Aspergillus niger and A. fumigatus. Structural elucidation of the synthesized compounds was realized based on various spectroscopic methods.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Acta Crystallographica, Section E: Crystallographic Communications called Crystal structure of 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline, Author is Jeyaseelan, S.; Rajegowda, H. R.; Britto Dominic Rayan, R.; Raghavendra Kumar, P.; Palakshamurthy, B. S., which mentions a compound: 6684-39-5, SMILESS is ClC1=NC=C(C=C1)[S](=O)(=O)Cl, Molecular C5H3Cl2NO2S, HPLC of Formula: 6684-39-5.

The tetrahydropyridine ring of the quinoline system in the title compound, C14H13ClN2O2S, adopts a half-chair conformation with the bond-angle sum at the N atom being 350.0°. The dihedral angle between the least-squares planes of the two aromatic rings is 50.13 (11)°. In the crystal, inversion dimers linked by pairs of C-H···O hydrogen bonds generate R 2 2(10) loops. Addnl. intermol. C-H···O hydrogen bonds generate C(7) chains along [100].

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Computed Properties of C5H3Cl2NO2S. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Chloro-5-pyridinesulfonyl chloride, is researched, Molecular C5H3Cl2NO2S, CAS is 6684-39-5, about Regioselective Synthesis of Sulfonyl-Containing Benzyl Dithiocarbamates through Copper-Catalyzed Thiosulfonylation of Styrenes. Author is Lai, Miao; Wu, Zhiyong; Li, Shi-Jun; Wei, Donghui; Zhao, Mingqin.

An efficient approach for the preparation of sulfonyl-containing benzyl dithiocarbamates has been developed using tetraalkylthiuram disulfides as the thiolating agents and sulfonyl chlorides as the sulfonyl sources in the presence of the copper catalyst. The dithiocarbamate group together with the sulfonyl group was simultaneously introduced into styrene in chemo- and regioselective manners. This protocol provides a convenient procedure, with good yields and functional group tolerance to various important sulfonyl-containing benzyl dithiocarbamates.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Triarylpyridylmethanes》. Authors are Adams, Roger; Hine, Jack; Campbell, John.The article about the compound:2-Chloro-5-pyridinesulfonyl chloridecas:6684-39-5,SMILESS:ClC1=NC=C(C=C1)[S](=O)(=O)Cl).Related Products of 6684-39-5. Through the article, more information about this compound (cas:6684-39-5) is conveyed.

The Na salt of 2-hydroxypyridine (I) and p-O2NC6H4SO2Cl give 80% 2-pyridyl p-nitrobenzenesulfonate, m. 157-60° (m.ps. corrected). 2-Pyridyl benzoate (11.1 g.) and 27 g. AlCl3, heated 3 hrs. at 180°, give 0.8% 5-benzoyl-2-hydroxypyridine, m. 194-6°; this was prepared in 66% yield from 2-hydroxy-5-pyridinecarboxylic acid through the acid chloride. 1-Methyl-2-pyridone-5-sulfonic acid (13.5 g.) and 26 g. PCl5, heated 2 hrs. at 125°, give 76% of the acid chloride, m. 50-1°; amide (II) m. 157-9°. 2-Chloro-N-2-pyridyl-5-pyridinesulfonamide, prepared in 66% yield from 2-chloro-5-pyridinesulfonyl chloride and 2-aminopyridine in C6H6, m. 237-9°. II and MeONa in MeOH, refluxed 60 hrs., give 77% 2-methoxy-5-pyridinesulfonamide, m. 149-50°. The melt of I (3 g.) and 3 g. Ph3COH, treated with 2 drops concentrated H2SO4 and heated 20 min. at 250°, gives 48% 5-(triphenylmethyl)-2-hydroxypyridine (IV), m. 365-8°; 3-Me derivative m. 260-2°, 54%; the 5-[(4-biphenylyl)diphenylmethyl] analog of IV m. 298-300°, 58%; its 3-Me derivative m. 307-10°, 56%. The same compounds result from Ph3CCl without catalyst. 6-Methyl-2-hydroxypyridine and Ph3COH give 22% (Ph3CCl gives 9%) 3-(triphenylmethyl)-6-methyl-2-hydroxypyridine, m. 314-17°, which does not react with POCl3. IV and a 6-fold excess of POCl3, heated 48 hrs. on the steam bath (sealed tube), give 48% of the 2-chloro analog (V), m. 256-7°; 3-Me derivative m. 130° and then 151-2°, 92%; the 5-[(4-biphenylyl)diphenylmethyl] analog of V m. 182-3°, 95%; its 3-Me derivative m. 158-9°, 93%. V in absolute EtOH, reduced 6 hrs. over Raney Ni at 70°/45 lb., gives 66% 3-(triphenylmethyl)pyridine (VI), m. 269-70°; 5-Me derivative m. 153-4°, 83%; the 3-[(4-biphenylyl)diphenylmethyl] analog of VI m. 195-6°, 91%; its 5-Me derivative m. 188-9°, 91%. VI exhibits a marked phosphorescence after irradiation with ultraviolet light at room temperature; the greenish white afterglow lasts only 1 sec. The infrared absorption spectra of VI and CPh4 are similar. IV (0.8 g.), 0.67 g. ClCH2CO2H, and 0.85 g. KOH in 25 ml. absolute EtOH, refluxed 6 hrs., give 92% 1-(carboxymethyl)-5-(triphenylmethyl)-2(1H)-pyridone, m. 264-6°.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Wang, Wentian; Zhang, Lu; Morlock, Lorraine; Williams, Noelle S.; Shay, Jerry W.; De Brabander, Jef K. researched the compound: 2-Chloro-5-pyridinesulfonyl chloride( cas:6684-39-5 ).COA of Formula: C5H3Cl2NO2S.They published the article 《Design and Synthesis of TASIN Analogues Specifically Targeting Colorectal Cancer Cell Lines with Mutant Adenomatous Polyposis Coli (APC)》 about this compound( cas:6684-39-5 ) in Journal of Medicinal Chemistry. Keywords: preparation TASIN analog targeting colorectal cancer. We’ll tell you more about this compound (cas:6684-39-5).

Despite advances in targeted anticancer therapies, there are still no small-mol.-based therapies available that specifically target colorectal cancer (CRC) development and progression, the second leading cause of cancer deaths. We previously disclosed the discovery of truncating adenomatous polyposis coli (APC)-selective inhibitor 1 (TASIN-1), a small mol. that specifically targets colorectal cancer cells lines with truncating mutations in the adenomatous polyposis coli (APC) tumor suppressor gene through inhibition of cholesterol biosynthesis. Here, we report a medicinal chem. evaluation of a collection of TASIN analogs and activity against colon cancer cell lines and an isogenic cell line pair reporting on the status of APC-dependent selectivity. A number of potent and selective analogs were identified, including compounds with good metabolic stability and pharmacokinetic properties. The compounds reported herein represent a first-in-class genotype-selective series that specifically target apc mutations present in the majority of CRC patients and serve as a translational platform toward a targeted therapy for colon cancer.

There is still a lot of research devoted to this compound(SMILES：ClC1=NC=C(C=C1)[S](=O)(=O)Cl)COA of Formula: C5H3Cl2NO2S, and with the development of science, more effects of this compound(6684-39-5) can be discovered.

Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Name: 2-Chloro-5-pyridinesulfonyl chloride. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Chloro-5-pyridinesulfonyl chloride, is researched, Molecular C5H3Cl2NO2S, CAS is 6684-39-5, about An experimental and theoretical dipole moment study of 2-chloropyridine-5-sulfonyl chloride. Author is Lumbroso, H.; Montoneri, E.; Pappalardo, G. C..

Anal. of the dipole moment (2.00 D) of 2-chloropyridine-5-sulfonly chloride in benzene at 30° supported a model in which the C(5)-SCl group is rotated by 40° from the 2-chloro-1-pyridyl group. Such a model, with the S Cl atom close to the 1-azanitrogen atom, can be explained by interplay of 2 conflicting factors, namely sulfonylchloride-arene conjugation and lesser repulsion between 1 of the O atoms and the aza N atom.

There is still a lot of research devoted to this compound(SMILES：ClC1=NC=C(C=C1)[S](=O)(=O)Cl)Name: 2-Chloro-5-pyridinesulfonyl chloride, and with the development of science, more effects of this compound(6684-39-5) can be discovered.

Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 6684-39-5, is researched, Molecular C5H3Cl2NO2S, about Synthesis and biological evaluation of N-(7-indolyl)-3-pyridinesulfonamide derivatives as potent antitumor agents, the main research direction is pyridinesulfonamide indolyl derivative preparation antitumor.Category: chiral-nitrogen-ligands.

The synthesis and antitumor activity of E7070 analogs containing a 3-pyridinesulfonamide moiety is reported. E7070 was selected from our sulfonamide-based compound collections, currently undergoing Phase II clin. trials because of its tolerable toxicity profile and some antitumor responses in the Phase I setting. Of the analogs examined, ER-35745 (I), a 6-amino-3-pyridinesulfonamide derivative, demonstrated significant oral efficacy against the HCT116 human colon carcinoma xenograft in nude mice.

If you want to learn more about this compound(2-Chloro-5-pyridinesulfonyl chloride)Category: chiral-nitrogen-ligands, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(6684-39-5).

Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis