119043-16-2

Basic information

• Product Name: 4-{2-{[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)-carbonyl]-amino}-ethyl}-benzenesulfonyl chloride
• Synonyms: 4-{2-{[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)-carbonyl]-amino}-ethyl}-benzenesulfonyl chloride
• CAS NO: 119043-16-2
• Molecular Formula: C₁₆H₁₉ClN₂O₄S
• Molecular Weight: 370.85106
• Mol File: 119043-16-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Refractive Index: 1.577
• CAS DataBase Reference: 4-{2-{[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)-carbonyl]-amino}-ethyl}-benzenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-{2-{[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)-carbonyl]-amino}-ethyl}-benzenesulfonyl chloride(119043-16-2)
• EPA Substance Registry System: 4-{2-{[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)-carbonyl]-amino}-ethyl}-benzenesulfonyl chloride(119043-16-2)

Safety Data

• Hazardous Substances Data: 119043-16-2(Hazardous Substances Data)

Usage

Uses

4-[2-[[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)carbonyl]amino]ethyl]benzenesulfonyl Chloride is an intermediate in the synthesis of 4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide (E925045), which is an intermediate for the preparation of Glimepiride. Glimepiride is a sulfonylurea hypoglycemic agent, used as an antidiabetic.

InChI:InChI=1/C16H19ClN2O4S/c1-3-14-11(2)10-19(15(14)20)16(21)18-9-8-12-4-6-13(7-5-12)24(17,22)23/h4-7H,3,8-10H2,1-2H3,(H,18,21)

Upstream product

• 607-97-6 ethyl 2-ethyl-3-oxobutanoate 
• 1943-82-4 phenethyl isocyanate 
• 247098-17-5 ethyl-α-ethylacetoacetate cyanohydrin 
• 766-36-9 3-ethyl-4-methyl-3-pyrrolin-2-one 
• 247098-18-6 3-ethyl-4-methyl-2-oxo-N-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide 

Downstream Products

• 599174-28-4 C₃₂H₄₂N₄O₇S 
• 119018-29-0 N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide 

Relevant articles and documents

Glimepiride impurity and preparation method thereof

The invention provides a glimepiride impurity and a preparation method thereof. The chemical name of the impurity is ethyl 4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrrolin-1-formylamino)ethyl]benzenesulfonate. The preparation method comprises the following steps: A, reacting 3-ethyl-4-methyl-2-oxo-N-phenethyl-2, 5-dihydro-1H-pyrrol-1-amide with chlorosulfonic acid to obtain 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrrolin-1-formamido)-ethyl]-benzenesulfonyl chloride; B, reacting the 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrrolin-1-formamido)-ethyl]-benzenesulfonyl chloride with an ethanol solution of sodium ethoxide to obtain an impurity crude product; and C, adding the impurity crude product into a mixed solution of methyl isobutyl ketone and acetone for purification, and separating to obtain the impurity. The purity of the prepared impurity can reach 99.5% or above, and the impurity can be used as an impurity reference substance for glimepiride bulk drug or preparation quality control.

Preparation method of glimepiride intermediate

The invention relates to a preparation method of a glimepiride intermediate compound I, and belongs to the technical field of preparation of raw material medicines. The preparation method comprises the following steps: reacting a compound II with diphenyl carbonate under the catalysis of an alkali (referring to Synlett, 28(18), 2495-2498; 2017) to prepare a compound IX; and adding a compound IX and 4-(2-aminoethyl)benzenesulfonamide according to a ratio of 1:1, adding a weak acid, adding isopropanol, and performing heating for a refluxing reaction. The invention provides the preparation methodof the glimepiride intermediate with a high purity.

A NOVEL PROCESS FOR PREPARATION OF SUBSTANTIALLY PURE GLIMEPIRIDE

The present invention discloses a novel process for purification of trans-4-methyl cyclohexylamine HC1 and 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide used in the synthesis of 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans-4-methyl cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide(I), popularly known as Glimepiride. The present invention also discloses a novel purification of Glimepiride Form I (I), having the undesired cis isomer below 0.15%. Glimepiride (I) is useful in the treatment of diabetes mellitus.