75028-24-9

Basic information

• Product Name: (Z)-2-(5-AMino-1,2,4-thiadiazol-3-yl)-2-ethoxyiMinoacetic acid
• Synonyms: (Z)-2-(5-AMino-1,2,4-thiadiazol-3-yl)-2-ethoxyiMinoacetic acid;(Z)-5-Amino-alpha-(ethoxyimino)-1,2,4-thiadiazole-3-acetic acid;(2Z)-(ethoxyiMino)-2-(5-aMino-1,2,4-thiadiazol-3-yl)-acetic acid;2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid;-2-(5-Amino-1,2,4-thiadiazol-3-yl);-2-(ethoxyimino);1,2,4-Thiadiazole-3-acetic acid, 5-amino-α-(ethoxyimino)-, (αZ)-;(Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic
• CAS NO: 75028-24-9
• Molecular Formula: C₆H₈N₄O₃S
• Molecular Weight: 216.21772
• EINECS: 1312995-182-4
• Mol File: 75028-24-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 430.5±28.0 °C(Predicted)
• Appearance: /
• Density: 1.71
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.44±0.41(Predicted)
• CAS DataBase Reference: (Z)-2-(5-AMino-1,2,4-thiadiazol-3-yl)-2-ethoxyiMinoacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-(5-AMino-1,2,4-thiadiazol-3-yl)-2-ethoxyiMinoacetic acid(75028-24-9)
• EPA Substance Registry System: (Z)-2-(5-AMino-1,2,4-thiadiazol-3-yl)-2-ethoxyiMinoacetic acid(75028-24-9)

Safety Data

• Hazardous Substances Data: 75028-24-9(Hazardous Substances Data)

Usage

Uses

(Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic Acid is an important intermediate for the preparation of Ceftaroline which possesses antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and P. aeruginosa.

Upstream product

• 1618104-04-3 (Z)-N-(3-(2-acetamido-1-(ethoxyimino)-2-oxoethyl)-1,2,4-thiadiazol-5-yl)pivalamide 
• 113080-37-8 (Z)-2-(5-amino-1,2,4-thiadiazole-3-yl)-2-ethoxyiminoacetonitrile 
• 84981-58-8 ethoxymethylenemalononitrile 
• 57967-25-6 2-cyano-2-ethoxyiminoacetamide 
• 344302-24-5 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino) acetonitrile 

Downstream Products

• 90211-01-1 2-[[5-(dichlorophosphinyl)amino]-1,2,4-thiadiazole-3-yl]-2(Z)-ethoxyiminoacetyl chloride 
• 142266-02-2 p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylate 
• 106962-96-3 benzhydryl 2-<(4S)-4-<2-(5-amino-1,2,4-thiadiazol-3-yl)-(Z)-2-(ethoxyimino)acetylamino>-3-oxo-2-isoxazolidinyl>-5-oxo-2-tetrahydrofurancarboxylate 

Relevant articles and documents

(Z) - 2 - (5- two chlorine phosphinylidynes amino -1, 2, 4-thiadiazol-3-yl) - 2-ethoxy imidogen acetyl chloride preparation method (by machine translation)

The invention relates to a preparation method of (Z)-2-(5-dichlorophosphorylamino-1,2,4-thiadiazolyl-3-yl)-2-ethoxyiminoacetyl chloride. The invention discloses a preparation method of ceftaroline fosamil side chain ATDE-Cl, which comprises the following steps: oximation reaction, dehydration reaction, ammonification reaction, cyclization reaction, hydrolysis reaction and acyl-chlorination reaction. The method has the advantages of short reaction steps, accessible raw materials and high yield; and the content of the prepared ceftaroline fosamil is higher than 93%, thereby conforming to the requirements for medicinal intermediates and satisfying the demands for ceftaroline fosamil production. The preparation method is low in cost, and can create considerable economic benefits for the enterprise.

An improved synthesis of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2- (ethoxyimino) acetic acid

An improved synthetic route of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2- (ethoxyimino)acetic acid (2a), an important intermediate for the preparation of Ceftaroline, from N-(3-aminoisoxazol-5-yl)acetamide (8) in total yield of 47% has been developed. The key intermediate (Z)-N-(3-(2-acetamido-1-(ethoxyimino)- 2-oxoethyl)-1,2,4-thiadiazol-5- yl)pivalamide (12a) was easily isolated from (Z/E)-N-(3-(2-acetamido-1-(ethoxyimino)-2-oxoethyl)-1,2,4 -thiadiazol-5- yl)pivalamide. The title compound 2a was obtained from the hydrolysis of 12a with a yield of 83%, and its structure was comfirmed by X-ray single crystal diffraction analysis. Moreover, (E)- and (Z)-N-(3-(2-acetamido-1-(ethoxyimino)-2 -oxoethyl)-1,2,4-thiadiazol-5-yl)pivalamide were prepared respectively from the etherification of oxime hydroxyl group under different conditions. This improved procedure has many appealing attributes such as convenient separation, good yields, and easy access to large scale.