Methyl 6-{[(4-methylphenyl)sulfonyl]imino}-3(1H)-pyridinecarboxylate

Base Information

• Chemical Name: Methyl 6-{[(4-methylphenyl)sulfonyl]imino}-3(1H)-pyridinecarboxylate
• CAS No.: 209971-44-8
• Molecular Formula: C14H14N2O4S
• Molecular Weight: 306.342
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID50377350
• Nikkaji Number: J2.831.273C
• Wikidata: Q82166538
• Mol file: 209971-44-8.mol

Synonyms:209971-44-8;Methyl 6-{[(4-methylphenyl)sulfonyl]imino}-3(1H)-pyridinecarboxylate;methyl 6-(4-methylphenylsulfonamido)nicotinate;methyl 6-[(4-methylphenyl)sulfonylamino]pyridine-3-carboxylate;SCHEMBL246879;DTXSID50377350;QHLDZCPKBKBYKO-UHFFFAOYSA-N;MFCD06200981;AKOS005070807;AKOS016568151;AKOS022182443;AKOS030245144;CS-0449827;methyl6-(4-methylphenylsulfonamido)nicotinate;Methyl 6-((4-methylphenyl)sulfonamido)nicotinate;6X-0714;J-522518;6-(Tosylamino)pyridine-3-carboxylic acid methyl ester;Methyl 6-(tosylimino)-1,6-dihydropyridine-3-carboxylate;Methyl 6-{[(4-methylphenyl)sulphonyl]imino}-1H-pyridine-3-carboxylate;methyl (6Z)-6-[(4-methylbenzenesulfonyl)imino]-1,6-dihydropyridine-3-carboxylate

Chemical Property of Methyl 6-{[(4-methylphenyl)sulfonyl]imino}-3(1H)-pyridinecarboxylate

Chemical Property:

• Melting Point: 214-216°C
• PSA: 96.97000
• LogP: 2.48010
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 306.06742811
• Heavy Atom Count: 21
• Complexity: 452

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 6-{[(4-methylphenyl)sulfonyl]imino}-1H-pyridine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC2=NC=C(C=C2)C(=O)OC

Technology Process of Methyl 6-{[(4-methylphenyl)sulfonyl]imino}-3(1H)-pyridinecarboxylate

There total 3 articles about Methyl 6-{[(4-methylphenyl)sulfonyl]imino}-3(1H)-pyridinecarboxylate 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: 93.0%

methyl 6-aminonicotinoate (36052-24-1) + p-toluenesulfonyl chloride (98-59-9) → 6-[(Z)-Toluene-4-sulfonylimino]-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (209971-44-8)

Guidance literature:

With pyridine; at 80 - 90 ℃;

DOI:10.1055/s-1998-2078

Reference yield: 91.0%

methyl 6-bromonicotinate (26218-78-0) + toluene-4-sulfonamide (70-55-3) → methyl 6-(4-methylphenylsulfonamido)nicotinate (209971-44-8)

Guidance literature:

With copper(l) iodide; potassium carbonate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In N,N-dimethyl-formamide; at 20 - 100 ℃;

DOI:10.1021/ol100263r

Reference yield:

methyl 6-aminonicotinoate (36052-24-1) + p-toluenesulfonyl chloride (98-59-9) → methyl 6-(4-methylphenylsulfonamido)nicotinate (209971-44-8)

Guidance literature:

With pyridine; at 80 ℃; for 16h;

upstream raw materials:

methyl 6-aminonicotinoate

p-toluenesulfonyl chloride

methyl 6-bromonicotinate

toluene-4-sulfonamide

Downstream raw materials:

methyl 1-(2-amino-2-oxoethyl)-6-(4-methylphenylsulfonamido)-1,6-dihydropyridine-3-carboxylate

3-(4-Chloro-phenylsulfanyl)-2-(2,2,2-trifluoro-acetylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

3-(4-Fluoro-phenylsulfanyl)-2-(2,2,2-trifluoro-acetylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

3-(3-Chloro-phenylsulfanyl)-2-(2,2,2-trifluoro-acetylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

Refernces

• 1、 Baffoe, Jonathan,Hoe, Madelene Y.,Barry Tou Re. "Copper-mediated n-heteroarylation of primary sulfonamides: Synthesis of mono-n-heteroaryl sulfonamides". supporting information; experimental part. p. 1532 - 1535. Retrieved 2010/06/19.