64987-16-2

Basic information

• Product Name: METHYL 2-AMINO-4-THIAZOLEACETATE
• Synonyms: (2-AMINO-THIAZOL-4-YL)-ACETIC ACID METHYL ESTER;METHYL 2-AMINOTHIAZOLE-4-ACETATE;METHYL 2-AMINO-4-THIAZOLEACETATE;METHYL 2-(2-AMINO-1,3-THIAZOL-4-YL)ACETATE;Methyl 2-aMinothiazol-4-yl-acetate;METHYL (2-AMINO-4-THIAZOLYL)ACETATE;METHYL (2-AMINO-4-THIAZOLYL)ACETATE, PURISS, 98%;2-Amino-4-(methylcarboxymethyl)-1,3-thiazole
• CAS NO: 64987-16-2
• Molecular Formula: C₆H₈N₂O₂S
• Molecular Weight: 172.2
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiazoles
• Mol File: 64987-16-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 112-116 °C(lit.)
• Boiling Point: 307.3 °C at 760 mmHg
• Flash Point: 139.7 °C
• Appearance: /
• Density: 1.353 g/cm³
• Vapor Pressure: 0.00073mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.61±0.10(Predicted)
• CAS DataBase Reference: METHYL 2-AMINO-4-THIAZOLEACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-AMINO-4-THIAZOLEACETATE(64987-16-2)
• EPA Substance Registry System: METHYL 2-AMINO-4-THIAZOLEACETATE(64987-16-2)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 64987-16-2(Hazardous Substances Data)

Usage

Uses

Methyl 2-Amino-4-thiazoleacetate is a reactant in the preparation of N-[4-(substituted)-1,3-thiazol-2-yl]-2-(substituted)acetamides as antibacterial agents against S. aureus, E. coli, P. aeruginosa, and K. pneumonia.

InChI:InChI=1/C6H8N2O2S/c1-10-5(9)2-4-3-11-6(7)8-4/h3H,2H2,1H3,(H2,7,8)

Synthetic route

methanol (67-56-1) + 2-amino-4-thiazoleacetic acid (29676-71-9) → (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2)

Conditions	Yield
Stage #1: methanol; 2-amino-4-thiazoleacetic acid With sulfuric acid In methanol at 0℃; Reflux; Stage #2: With sodium hydrogencarbonate pH=8 - 9;	93%
Stage #1: methanol; 2-amino-4-thiazoleacetic acid With sulfuric acid at 0 - 5℃; for 5h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water pH=8 - 9;	93%
With thionyl chloride for 12h;	91%

Methyl 4-chloroacetoacetate (32807-28-6) + thiourea (17356-08-0) → (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2)

Conditions	Yield
In ethanol Reflux;	89.5%
With ethanol Reflux;	89.5%
In ethanol for 4h; Heating;

2-amino-4-thiazoleacetic acid (29676-71-9) + diazomethyl-trimethyl-silane (18107-18-1) → (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2)

Conditions	Yield
In methanol; benzene at 20℃;

trityl chloride (76-83-5) + (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) → methyl 2-tritylamino-4-thiazolylacetate (78287-71-5)

Conditions	Yield
With triethylamine In dichloromethane for 15h;	96%

(2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) + methyl iodide (74-88-4) → methyl (2-imino-3-methyl-2,3-dihydrothiazol-4-yl)acetate hydroiodide (1586872-68-5)

Conditions	Yield
In tetrahydrofuran at 20℃; for 72h;	93%

di-tert-butyl dicarbonate (24424-99-5) + (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) → methyl 2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetate (103053-96-9)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 90℃;	79%
In toluene at 85℃; for 24h;
In toluene at 85℃; for 24h;
at 85℃; for 24h;

4,5-dibromopyrrol-2-yl trichloromethyl ketone (50371-52-3) + (2-amino-thiazol-4-yl)-acetic acid methyl ester (64987-16-2) → methyl 2-(2-(4,5-dibromo-1H-pyrrole-2-carboxamido)thiazol-4-yl)acetate

Conditions	Yield
Stage #1: (2-amino-thiazol-4-yl)-acetic acid methyl ester With sodium carbonate In N,N-dimethyl-formamide Stage #2: 4,5-dibromopyrrol-2-yl trichloromethyl ketone In N,N-dimethyl-formamide at 80℃;	77%
Stage #1: (2-amino-thiazol-4-yl)-acetic acid methyl ester With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 4,5-dibromopyrrol-2-yl trichloromethyl ketone In N,N-dimethyl-formamide at 80℃;	77%

Upstream product

• 67-56-1 methanol 
• 29676-71-9 2-amino-4-thiazoleacetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 32807-28-6 Methyl 4-chloroacetoacetate 
• 17356-08-0 thiourea 

Downstream Products

• 681138-10-3 4'-O-demethyl-4β-[4''-(methyl-O-acetyl)-2''-thiazolylamino]-4-desoxypodophyllotoxin 
• 1416811-05-6 C₂₃H₁₈Cl₂FN₃O₄S 
• 1416810-89-3 C₂₃H₂₅Cl₂N₃O₄S 
• 263169-24-0 2-(2-bromothiazol-4-yl)ethanol 
• 62557-05-5 2-(2-methanesulfonamidothiazol-4-yl)-acetic acid 
• 89336-46-9 2-{2[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl}acetic acid 
• 1610728-72-7 N,N'-(5,5'-((1S,3S)-cyclohexane-1,3-diyl)bis(1,3,4-thiadiazole-5,2-diyl))bis(2-(2-methoxythiazol-4-yl)acetamide) 
• 1324935-54-7 methyl 2-(2-(2-(3-methoxyphenyl)acetamido)thiazol-4-yl)acetate 
• 1390409-52-5 methyl 2-(2-(2-m-tolylacetamido)thiazol-4-yl)acetate 
• 1154358-30-1 methyl 2-(2-(2-p-tolylacetamido)thiazol-4-yl)acetate 
• 56826-61-0 (2-methylpyridin-3-yl)methanol 
• 1421928-97-3 methyl 2-(2-(((2-methylpyridin-3-yl)methyl)amino)thiazol-4-yl)acetate 
• 64220-26-4 [2-[(triphenyl-methyl)-amino]-thiazol-4-yl] acetic acid 
• 1351823-25-0 C₄₆H₄₆N₄O₄S₂ 

Relevant articles and documents

Design, synthesis and biological evaluation of 4,5-dibromo-N-(thiazol-2-yl)-1H-pyrrole-2-carboxamide derivatives as novel DNA gyrase inhibitors

Development of novel DNA gyrase B inhibitors is an important field of antibacterial drug discovery whose aim is to introduce a more effective representative of this mechanistic class into the clinic. In the present study, two new series of Escherichia coli DNA gyrase inhibitors bearing the 4,5-dibromopyrrolamide moiety have been designed and synthesized. 4,5,6,7-Tetrahydrobenzo[1,2-d]thiazole-2,6-diamine derivatives inhibited E. coli DNA gyrase in the submicromolar to low micromolar range (IC50values between 0.891 and 10.4 μM). Their “ring-opened” analogues, based on the 2-(2-aminothiazol-4-yl)acetic acid scaffold, displayed weaker DNA gyrase inhibition with IC50values between 15.9 and 169 μM. Molecular docking experiments were conducted to study the binding modes of inhibitors.

NLRP MODULATORS

In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured: or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula A can be as defined anywhere herein, useful to treat connected to the modulation of NRLP3.

COMPOUNDS AND THEIR METHODS OF USE

Compounds and compositions comprising compounds that inhibit glutaminase are described herein. Also described herein are methods of using the compounds that inhibit glutaminase in the treatment of cancer.