40283-46-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Aminothiazole-5-carboxylic acid is used as a building block for the synthesis of pharmaceuticals, leveraging its heterocyclic structure to contribute to the development of new drugs with diverse therapeutic applications. Its presence in drug molecules can enhance their pharmacological properties, such as potency, selectivity, and bioavailability.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Aminothiazole-5-carboxylic acid is utilized as a starting material for the preparation of agrochemicals, including pesticides and herbicides. Its incorporation into these compounds can improve their effectiveness in controlling pests and weeds, thereby increasing crop yields and protecting agricultural investments.
Used in Heterocyclic Chemistry:
2-Aminothiazole-5-carboxylic acid is used as a starting material for the preparation of various heterocyclic compounds with potential biological activity. Its unique combination of functional groups allows for the creation of novel chemical entities that can be explored for their potential applications in medicinal chemistry, materials science, and other areas of research.
Used in Antimicrobial Applications:
2-Aminothiazole-5-carboxylic acid has been studied for its potential antimicrobial properties, making it a candidate for use in applications aimed at combating bacterial infections. Its ability to inhibit microbial growth can be harnessed in the development of new antimicrobial agents, particularly in an era where antibiotic resistance is a growing concern.
Used in Antifungal Applications:
Similarly, the compound has demonstrated antifungal properties, positioning it as a potential agent in the fight against fungal infections. Its use in antifungal formulations could provide new treatment options for a variety of fungal diseases, improving patient outcomes and addressing the need for novel antifungal therapies.
Used in Antitumor Applications:
The antitumor potential of 2-Aminothiazole-5-carboxylic acid has been a subject of interest, with studies exploring its ability to inhibit tumor growth and proliferation. Its use in oncology could lead to the development of new therapeutic agents for cancer treatment, offering alternative strategies to conventional chemotherapy and potentially improving patient response rates and survival outcomes.

InChI:InChI=1/C4H4N2O2S/c5-4-6-1-2(9-4)3(7)8/h1H,(H2,5,6)(H,7,8)

Synthetic route

2-amino-thiazole-5-carboxylic acid ethyl ester (32955-21-8) → 2-aminothiazole-5-carboxylic acid (40283-46-3)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water Reflux;	86%
With sodium hydroxide
With barium dihydroxide
With potassium hydroxide In methanol

methyl 2-aminothiazole-5-carboxylate (6633-61-0) → 2-aminothiazole-5-carboxylic acid (40283-46-3)

Conditions	Yield
With sodium hydroxide Ambient temperature;	74%

2-acetylamino-thiazole-5-carbonitrile (99903-61-4) → 2-aminothiazole-5-carboxylic acid (40283-46-3)

Conditions	Yield
With hydrogenchloride

2-aminothiazole-5-carboxylic acid (40283-46-3) + acetic anhydride (108-24-7) → 2-(acetylamino)thiazole-5-carboxylic acid (1170060-19-1)

Conditions	Yield
With pyridine at 20 - 130℃;	71%

2-aminothiazole-5-carboxylic acid (40283-46-3) → 5-fluoro-1,3-thiazol-2-amine hydrochloride (745053-64-9)

Conditions	Yield
Stage #1: 2-aminothiazole-5-carboxylic acid With potassium phosphate In 1,4-dioxane; methanol; toluene at 20℃; for 2h; Stage #2: With 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate In 1,4-dioxane; methanol; toluene at 20℃; for 0.5h; Stage #3: With hydrogenchloride In 1,4-dioxane; methanol; toluene Product distribution / selectivity;	69%

formaldehyd (50-00-0) + 2-aminothiazole-5-carboxylic acid (40283-46-3) + 3-aminopyrazinoic acid (5424-01-1) → 2-(4-oxopteridin-3(4H)-yl)thiazole-5-carboxylic acid

Conditions	Yield
In ethanol for 6h; Reflux;	44%

2-aminothiazole-5-carboxylic acid (40283-46-3) + dibenzylamine (103-49-1) → 2-amino-N,N-dibenzylthiazole-5-carboxamide

Conditions	Yield
Stage #1: 2-aminothiazole-5-carboxylic acid With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: dibenzylamine In N,N-dimethyl-formamide at 20℃;	41%

2-aminothiazole-5-carboxylic acid (40283-46-3) + (aminomethyl)cyclopropane hydrochloride (7252-53-1) → N-cyclopropylmethyl-2-aminothiazole-5-carboxamide (1152209-96-5)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃;

2-aminothiazole-5-carboxylic acid (40283-46-3) + 1-cyclopentylethyl amine hydrochloride (150812-09-2) → N-(1-cyclopentylethyl)-2-aminothiazole-5-carboxamide (1152210-00-8)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃;

2-aminothiazole-5-carboxylic acid (40283-46-3) + cyclopropylmethyl-amine hydrochloride → N-cyclopentylmethyl-2-aminothiazole-5-carboxamide (1152210-06-4)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃;

2-aminothiazole-5-carboxylic acid (40283-46-3) + di-tert-butyl dicarbonate (24424-99-5) → 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid (302964-02-9)

Conditions	Yield
Stage #1: 2-aminothiazole-5-carboxylic acid; di-tert-butyl dicarbonate With sodium hydroxide In tetrahydrofuran; water at 0 - 25℃; for 24h; Industry scale; Stage #2: With acetic acid In tetrahydrofuran; water at 0 - 5℃; for 1h; pH=4.9; Industry scale;

2-aminothiazole-5-carboxylic acid (40283-46-3) + (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinoline-1(2H)-one (1350643-72-9) → (S)-2-amino-N-(1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)thiazole-5-carboxamide (1466563-34-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

2-aminothiazole-5-carboxylic acid (40283-46-3) + (S)-2-((S)-2-amino-4-phenylbutanamido)-4-methyl-N-((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)pentanamide 2,2,2-trifluoroacetate → C38H50N6O6S (1545468-62-9)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃;

2-aminothiazole-5-carboxylic acid (40283-46-3) + N,N-diethylaniline (91-66-7) → C14H16N4O2S

Conditions	Yield
Stage #1: 2-aminothiazole-5-carboxylic acid With phosphoric acid; sulfuric acid; sodium nitrite In water at -5 - 0℃; for 5h; Stage #2: N,N-diethylaniline With sodium hydroxide In water at -5 - 0℃; for 3h;

2-aminothiazole-5-carboxylic acid (40283-46-3) + isobutyric Acid (79-31-2) → 2-isobutyramidothiazole-5-carboxylic acid

Conditions	Yield
at 100℃;

Upstream product

• 32955-21-8 2-amino-thiazole-5-carboxylic acid ethyl ester 
• 99903-61-4 2-acetylamino-thiazole-5-carbonitrile 
• 6633-61-0 methyl 2-aminothiazole-5-carboxylate 

Downstream Products

• 40283-47-4 N-(2-amino-thiazole-5-carbonyl)-glutamic acid diethyl ester 
• 59521-24-3 2-Nitro-5-thiazolcarbonsaeure 
• 96-50-4 2-thiazolylamine 
• 1170060-19-1 2-(acetylamino)thiazole-5-carboxylic acid 
• 1466563-34-7 (S)-2-amino-N-(1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)thiazole-5-carboxamide 
• 64588-82-5 5-fluoro-1,3-thiazol-2-amine 
• 745053-64-9 5-fluoro-1,3-thiazol-2-amine hydrochloride 
• 302964-02-9 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid 

Relevant academic research and scientific papers

Discovery of the first inhibitors of bacterial enzyme D-aspartate ligase from Enterococcus faecium (Aslfm)

The D-aspartate ligase of Enterococcus faecium (Aslfm) is an attractive target for the development of narrow-spectrum antibacterial agents that are active against multidrug-resistant E. faecium. Although there is currently little available information regarding the structural characteristics of Aslfm, we exploited the knowledge that this enzyme belongs to the ATP-grasp superfamily to target its ATP binding site. In the first design stage, we synthesized and screened a small library of known ATP-competitive inhibitors of ATP-grasp enzymes. A series of amino-oxazoles derived from bacterial biotin carboxylase inhibitors showed low micromolar activity. The most potent inhibitor compound 12, inhibits Aslfm with a Ki value of 2.9 μM. In the second design stage, a validated ligand-based pharmacophore modeling approach was used, taking the newly available inhibition data of an initial series of compounds into account. Experimental evaluation of the virtual screening hits identified two novel structural types of Aslfm inhibitors with 7-amino-9H-purine (18) and 7-amino-1H-pyrazolo[3,4-d]pyrimidine (30 and 34) scaffolds, and also with Ki values in the low micromolar range. Investigation the inhibitors modes of action confirmed that these compounds are competitive with respect to the ATP molecule. The binding of inhibitors to the target enzyme was also studied using isothermal titration calorimetry (ITC). Compounds 6, 12, 18, 30 and 34 represent the first inhibitors of Aslfm reported to date, and are an important step forward in combating infections due to E. faecium.

Studies on Decarboxylation Reactions. Part 7. Kinetic Study of the Decarboxylation of 2-Amino- and 2-Phenylamino-thiazole-5-carboxylic Acids

The rate constants of the decarboxylation reaction of 2-amino- and 2-phenylamino-thiazole-5-carboxylic acid (3a-b), and, for comparison, of 5-phenylamino-1,3,4-thiadiazole-2-carboxylic acid (2b) have been measured in water over a range of proton activities.The results obtained suggest: (i) compound 2b decarboxylates, in the whole range of proton activity studied, through a unimolecular decarboxyprotonation mechanism characteristic of 1,3,4-oxa- and 1,3,4-thiadiazole derivatives; (ii) in contrast, 3a-b decarboxylate via either a unimolecular decarboxyprotonation or a bimolecular protiodecarboxylation mechanism as a function of proton activity.