ChemicalBook CAS DataBase List Glimepiride

Glimepiride synthesis

4synthesis methods

Product Name:Glimepiride
CAS Number:93479-97-1
Molecular formula:C24H34N4O5S
Molecular Weight:490.62

Glimepiride is a new generation of sulfonylurea hypoglycemic drugs and used to treat type 2 diabetes that cannot be controlled by diet and exercise. It is the first FDA-approved sulfonylurea for use with insulin. Preparation of glimepiride: 3-ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrole is reacted with phenethyl isocyanate, and then chlorosulfonated with chlorosulfonic acid , aminolysis to sulfonamide, and finally condensation with p-methylcyclohexyl isocyanate to obtain the product.

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Yield:-

Steps:

Multi-step reaction with 4 steps
1.1: toluene / 2 h / 120 - 130 °C / Industrial scale
2.1: chlorosulfonic acid / dichloromethane / -5 - 30 °C
3.1: ammonium hydroxide / methanol / 2 h / 20 - 30 °C / Industrial scale
4.1: potassium carbonate / acetonitrile / 6 h / 50 - 60 °C
4.2: 4 h / 70 - 75 °C

References:

Jiangxi Learned Xinhe Pharmaceutical Co., Ltd.;Xie Xiping;Leng Zhi;Liu Yi;Yin Qinghua;Zhang Zuofang;Ye Gang CN108383768, 2018, A

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