74370-93-7

Basic information

• Product Name: 2-AMINO-4-TERT-BUTYLTHIAZOLE
• Synonyms: TIMTEC-BB SBB004015;BUTTPARK 44\03-55;2-AMINO-4-TERT-BUTYLTHIAZOLE;AKOS BBS-00000450;4-TERT-BUTYL-1,3-THIAZOL-2-AMINE;4-TERT-BUTYL-1,3-THIAZOL-2-YLAMINE;4-TERT-BUTYL-THIAZOL-2-YLAMINE;2-Amino-4-(tert-butyl)-1,3-thiazole
• CAS NO: 74370-93-7
• Molecular Formula: C₇H₁₂N₂S
• Molecular Weight: 156.25
• Mol File: 74370-93-7.mol

Chemical Properties

• Melting Point: 99-102 °C
• Boiling Point: 141-143℃ (20 Torr)
• Flash Point: 106.9 °C
• Appearance: /
• Density: 1.0909 (rough estimate)
• Vapor Pressure: 0.0185mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 5.53±0.10(Predicted)
• BRN: 114270
• CAS DataBase Reference: 2-AMINO-4-TERT-BUTYLTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-TERT-BUTYLTHIAZOLE(74370-93-7)
• EPA Substance Registry System: 2-AMINO-4-TERT-BUTYLTHIAZOLE(74370-93-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37-22
• Safety Statements: 39-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 74370-93-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H12N2S/c1-7(2,3)5-4-10-6(8)9-5/h4H,1-3H3,(H2,8,9)

Upstream product

• 5469-26-1 1-Bromopinacolon 
• 17356-08-0 thiourea 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 111559-56-9 [3-(2,2-Dimethyl-propionyl)-oxiranylmethyl]-phosphonic acid diethyl ester 
• 7257-96-7 3,3-dimethyl-1-(tosyloxy)butan-2-one 
• 6832-15-1 1-diazo-3,3-dimethyl-2-butanone 
• 3282-30-2 pivaloyl chloride 
• 13547-70-1 1-chloro-3,3-dimethyl-butan-2-one 

Downstream Products

• 82245-97-4 2-acetamido-4-t-butylthiazole 
• 96770-78-4 (4-tert-butyl-thiazol-2-yl)-trityl-amine 
• 82202-35-5 4-t-butyl-2-trichloroacetamidothiazole 
• 136860-32-7 4-tert-butyl-2-(4-methoxybenzylideneamino)thiazole 
• 136860-31-6 4-tert-butyl-2-<4-(dimethylamino)benzylideneamino>thiazole 
• 82202-32-2 5-bromo-4-tert-butylthiazol-2-amine 
• 881997-23-5 tert-butyl (2E)-3-(8-{[(4-tert-butyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(cyclohex-1-enyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)acrylate 
• 79932-34-6 diethyl 2-[(4-tert-butylthiazol-2-ylamino)methylene]malonate 
• 501921-68-2 C₂₄H₂₂ClN₃O₂S 
• 1208552-82-2 C₁₈H₂₃ClN₂OS 
• 1218791-53-7 N-(4-tert-butylthiazol-2-yl)-2-(4-(methylsulfonyl)phenyl)-3-(tetrahydro-2H-pyran-4-yl)-propanamide 
• 884340-25-4 phenyl 4-tert-butylthiazol-2-ylcarbamate 
• 1363337-52-3 3-((4-(tert-butyl)thiazol-2-yl)amino)benzonitrile 
• 1363337-33-0 4-(tert-butyl)-N-(p-tolyl)thiazol-2-amine 

Relevant articles and documents

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system

A series of 2-aminothiazoles is prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus providing a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction.

Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Heterocyclic compounds as Weel inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

Method for preparing 2-aminothiazole compound

The invention discloses a method for preparing a 2-aminothiazole compound. The method comprises the following steps: in an organic solvent, carrying out a condensation reaction on thiourea representedby a formula (II) and a ketone compound represented by a formula (III) at 50-120 DEG C for 6-24 h under the catalysis of elemental iodine, and after the reaction is finished, carrying out post-treatment on the reaction solution to obtain the 2-aminothiazole compound represented by a formula (I). According to the invention, the method has characteristics of cheap and easily available reaction rawmaterials, mild reaction conditions, simpleness, no requirement of transition metal catalysts and a stoichiometric halogenating reagents and cost reducing, and can be used for synthesizing a series of2-aminothiazole derivatives, and the prepared products can be used as important intermediates for synthesizing thiazole structure-containing drugs or bioactive compounds.

Synthesis, Identification, and Structure-Activity Relationship Analysis of GATA4 and NKX2-5 Protein-Protein Interaction Modulators

Transcription factors GATA4 and NKX2-5 directly interact and synergistically activate several cardiac genes and stretch-induced cardiomyocyte hypertrophy. Previously, we identified phenylisoxazole carboxamide 1 as a hit compound, which inhibited the GATA4-NKX2-5 transcriptional synergy. Here, the chemical space around the molecular structure of 1 was explored by synthesizing and characterizing 220 derivatives and structurally related compounds. In addition to the synergistic transcriptional activation, selected compounds were evaluated for their effects on transcriptional activities of GATA4 and NKX2-5 individually as well as potential cytotoxicity. The structure-activity relationship (SAR) analysis revealed that the aromatic isoxazole substituent in the southern part regulates the inhibition of GATA4-NKX2-5 transcriptional synergy. Moreover, inhibition of GATA4 transcriptional activity correlated with the reduced cell viability. In summary, comprehensive SAR analysis accompanied by data analysis successfully identified potent and selective inhibitors of GATA4-NKX2-5 transcriptional synergy and revealed structural features important for it.

An efficient PEG-400 mediated catalyst free green synthesis of 2-amino-thiazoles from α-diazoketones and thiourea

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from α-diazoketones using PEG-400 solvent system. This novel synthetic approach involves the reaction between thiourea and α-diazoketones in PEG-400 at 100 °C to yield the corresponding 2-aminothiazoles in good yields. The method is simple, rapid and generates thiazole derivatives in excellent yields without the use of any catalysts. This green protocol can be utilized for fast synthesis of various 2-aminothiazoles in good yields. [Figure not available: see fulltext.]

Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model

Psoriasis is a chronic T-cell-mediated autoimmune disease, and FMS-like tyrosine kinase 3 (FLT3) has been considered as a potential molecular target for the treatment of psoriasis. In this investigation, structural optimization was performed on a lead compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (1), which showed a moderate inhibitory activity againt FLT3. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis led to the discovery of a number of potent FLT3 inhibitors. One of the most active compounds, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (18b), was then chosen for in-depth antipsoriasis studies because this compound displayed the highest potency in a preliminary antipsoriasis test. Compound 18b exhibited significant antipsoriatic effects in the K14-VEGF transgenic mouse model of psoriasis, and no recurrence was found 15 days later after the last administration. Detailed mechanisms of action of compound 18b were also investigated. Collectively, compound 18b could be a potential drug candidate for psoriasis treatment.

Convenient and simple synthesis of 2-aminothiazoles by the reaction of α-halo ketone carbonyls with ammonium thiocyanate in the presence of N-methylimidazole

Substituted 2-aminothiazole derivatives were obtained as a result of N-methylimidazole catalyzed cyclization of α-halo ketone carbonyls with ammonium thiocyanate in water-alcoholic media. The generality of the method has been demonstrated by screening a series of aromatic/heteroaromatic/aliphatic α-halo ketones, α-halo β-diketones, and α-halo β-ketoesters. The developed method is simple, mild, and general route for the preparation of diversely functionalized 2-aminothiazoles in good to moderate yields from readily available starting materials.

Copper acetate-catalyzed, mild, highly efficient, and practical synthesis of thiazoles and aminothiazoles

A mild and highly efficient synthesis of thiazoles by the condensation of α-bromo ketones with thiourea in the presence of a catalytic amount of copper acetate at room temperature has been described. The method is applicable for a variety of aryl and alkyl α-bromo ketones. The catalyst is inexpensive, and substituted thiazoles are obtained in good yields.

First example of the coupling of α-diazoketones with thiourea: a novel route for the synthesis of 2-aminothiazoles

α-Diazoketones undergo smooth coupling with thiourea in the presence of 10 mol % of copper(II) triflate to produce the corresponding 2-aminothiazoles in excellent yields with high selectivity. The use of copper(II) triflate makes this method simple, convenient and practical. This method works well with both aryl and alkyl diazoketones to furnish a wide range of 2-aminothiazoles.