129639-79-8

Basic information

• Product Name: N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine
• Synonyms: N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine;Abafungin;BAY-W 6341;N-[4-[2-(2,4-Dimethylphenoxy)phenyl]-2-thiazolyl]-1,4,5,6-tetrahydro-2-pyrimidinamine
• CAS NO: 129639-79-8
• Molecular Formula: C21H22N4OS
• Molecular Weight: 378.49
• Mol File: 129639-79-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 199 °C
• Boiling Point: 533.6 °C at 760 mmHg
• Flash Point: 276.5 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 1.82E-11mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine(129639-79-8)
• EPA Substance Registry System: N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine(129639-79-8)

Safety Data

• Hazardous Substances Data: 129639-79-8(Hazardous Substances Data)

Usage

Description

N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine is a compound belonging to the class of guanidines. It is characterized by a tetrahydropyrimidin-2(1H)-imine structure, where the hydrogen of the imino group is replaced by a thiazol-2-yl group. This thiazol-2-yl group is further substituted by a 2-(2,4-dimethylphenoxy)phenyl group at position 4. This unique molecular structure endows it with potential applications in various fields.

Uses

1. Used in Antifungal Applications:
N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine is used as a broad-spectrum antifungal agent for the topical treatment of fungal nail infections. Its efficacy in targeting and treating fungal infections makes it a valuable compound in the field of dermatology and antifungal therapy.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine is used as a key intermediate in the synthesis of various therapeutic agents. Its unique chemical structure allows for the development of new drugs with potential applications in treating a wide range of diseases and conditions.
3. Used in Research and Development:
N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine is also utilized in research and development settings, where it serves as a valuable tool for understanding the mechanisms of action and potential interactions of various biological targets. Its use in research can lead to the discovery of new therapeutic strategies and the development of novel drugs with improved efficacy and safety profiles.

Originator

Abafungin,York Pharma

Manufacturing Process

15.8 g (0.12 mole) N-(1,4,5,6-tetrahydropyrimidinyl)thiourea were added to 27.45 g (0.1 mole) 2-(2,4-dimethylphenoxy)phenacyl chloride in 100 ml acetone and heated to reflux for 2 hours. On cooling the falling out product was filtered off, washed with acetone and dried. N-[4-[2-(2,4- Dimethylphenoxy)phenyl]-2-thiazolyl]-1,4,5,6-tetrahydro-2-pyrimidinamine hydrochloride was prepared. Yield 91.4%; MP: 160°C. 20.72 g (0.05 mole) above product was stirred with 300 ml 1 N sodium hydroxide for 30 minutes at room temperature. The insoluble product was filtered off, washed and dried. Yield of N-[4-[2-(2,4-dimethylphenoxy)phenyl]- 2-thiazolyl]-1,4,5,6-tetrahydro-2-pyrimidinamine was 16.2 g (86%). MP: 191°-192°C.

Therapeutic Function

Antibacterial, Antifungal

InChI:InChI=1/C21H22N4OS/c1-14-8-9-18(15(2)12-14)26-19-7-4-3-6-16(19)17-13-27-21(24-17)25-20-22-10-5-11-23-20/h3-4,6-9,12-13H,5,10-11H2,1-2H3,(H2,22,23,24,25)