5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide

Base Information

• Chemical Name: 5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide
• CAS No.: 33288-71-0
• Molecular Formula: C14H16N4O3S
• Molecular Weight: 320.372
• Hs Code.: 2935909550
• European Community (EC) Number: 608-855-7
• UNII: EBQ9973HL9
• DSSTox Substance ID: DTXSID00186914
• Nikkaji Number: J292.585K
• Wikidata: Q27277096
• Mol file: 33288-71-0.mol

Synonyms:33288-71-0;5-Methyl-N-(4-sulfamoylphenethyl)pyrazine-2-carboxamide;2-[4-Aminosulfonyl-phenyl]-ethyl-5-methylpyrazinecarboxamide;5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide;5-Methyl-N-(2-(4-sulfamoylphenyl)ethyl)pyrazine-2-carboxamide;UNII-EBQ9973HL9;EBQ9973HL9;5-Methyl-N-(4-sulfamoylphenethyl)-pyrazine-2-carboxamide;5-methyl-n-[2-(4-sulphamoylphenyl)ethyl]pyrazine-2-carboxamide;4-[beta-(5-Methylpyrazinyl-2-carboxamido)ethyl]benzene Sulfonamide;Pyrazinecarboxamide, N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methyl-;PYRAZINECARBOXAMIDE, N-(2-(4-(AMINOSULFONYL)PHENYL)ETHYL)-5-METHYL-;Glipizide Imp. A (EP);Glipizide USP Related Compound A;Glipizide USP RC A;5-Methyl-N-[2-(4-sulphamoylphenyl)ethyl]pyrazine-2-carboxamide;Glipizide Related Compound A;Glipizide Impurity A;Glipizide sulfonamide;Glipizide impurity A;SCHEMBL7826309;DTXSID00186914;IMEZLHZLIANIAS-UHFFFAOYSA-N;{2-[4-Aminosulphonyl-phenyl]-ethyl}-5-methylpyrazinecarboxamide;BCP13823;N-{2-[4-(aminosulfonyl)phenyl]ethyl}-5-methyl-2-pyrazinecarboxamide;AKOS007992962;CS-T-58541;AC-15563;GLIPIZIDE IMPURITY A [EP IMPURITY];GLIPIZIDE EP IMPURITY A (USP RC A);CS-0215413;FT-0672110;EN300-245286;A821712;Q27277096;Z30858000;4-[2-(5-methylpyrazine-2-carboxamide)ethyl]benzenesulfonamide;N-[4-(Aminosulfonyl)phenethyl]-5-methyl-2-pyrazinecarboxamide;PYRAZINECARBOXAMIDE, 5-METHYL-N-(P-SULFAMOYLPHENETHYL)-;4-[?-(5-Methylpyrazinyl-2-carboxamido)ethyl]benzene Sulfonamide;N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methylpyrazine-carboxamide;4-(2-(5-METHYLPYRAZINE-2-CARBOXAMIDO)ETHYL)BENZENESULFONAMIDE;4-(2-(5-METHYLPYRAZINYL-2-CARBOXAMIDO)ETHYL)BENZENESULFONAMIDE;N-(2-((4-AMINOSULFONYL)PHENYL)ETHYL)-5-METHYL-PYRAZINECARBOXAMIDE;4-(5-(3-methylbenzyl)-4,5,6,7-tetrahydrooxazolo[4,5-c]pyridin-2-yl)benzoic acid

Chemical Property of 5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 0-0Pa at 20-25℃
• Melting Point: 237-239 °C
• Refractive Index: 1.601
• PSA: 123.42000
• Density: 1.342 g/cm³
• LogP: 2.57690
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 320.09431156
• Heavy Atom Count: 22
• Complexity: 469

Purity/Quality:

99% ^*data from raw suppliers

4-[β-(5-Methylpyrazinyl-2-carboxamido)ethyl]benzeneSulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C=N1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N
• Uses: An intermediate in the synthesis of Glipizide (G410225). 4-[β-(5-Methylpyrazinyl-2-carboxamido)ethyl]benzene Sulfonamide (Glipizide EP Impurity A) is an intermediate in the synthesis of Glipizide (G410225).

Technology Process of 5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide

There total 12 articles about 5-methyl-N-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide 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: 98.0%

C13H10N2O4 + 4-(2-aminoethyl)benzenesulfonamide (35303-76-5) → N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide (33288-71-0)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/chem.202103196

Reference yield: 93.4%

2-methylpyrazin-5-carboxylic acid (5521-55-1) + N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea (2015-16-9) → N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide (33288-71-0)

Guidance literature:

2-methylpyrazin-5-carboxylic acid; With triethylamine; In acetone; at 0 ℃; for 1h;

With chloroformic acid ethyl ester; In acetone; for 1h;

N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea; With triethylamine; In acetone; at 20 ℃; for 3h;

DOI:10.1515/znb-2020-0134

Reference yield: 93.0%

2-methylpyrazin-5-carboxylic acid (5521-55-1) + 4-(2-aminoethyl)benzenesulfonamide (35303-76-5) → N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide (33288-71-0)

Guidance literature:

2-methylpyrazin-5-carboxylic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 40 - 50 ℃; for 1h; Large scale;

4-(2-aminoethyl)benzenesulfonamide; In N,N-dimethyl-formamide; at 0 - 10 ℃; for 1h; Solvent; Reagent/catalyst; Large scale;

upstream raw materials:

glipizide

5-methylpyrazine-2-carbonyl chloride

4-(2-aminoethyl)benzenesulfonamide

2-methylpyrazin-5-carboxylic acid

Downstream raw materials:

ethyl ({4-[2-(5-methylpyrazine-2-carboxamido)ethyl]phenyl}sulfonyl)carbamate

glipizide

Refernces

• 1、 Bui, Thi Thoi,Tran, Van Loc,Ngo, Dai Quang,Tran, Van Chien,Tran, Van Sung,Tran, Thi Phuong Thao. "Synthesis and evaluation of α-glucosidase inhibitory activity of sulfonylurea derivatives". . p. 163 - 171. Retrieved 2021/03/16.
• 2、 -. "NOVEL COMPOUNDS AND USES". Page/Page column 56. . Retrieved 2018/12/13.