Heterocyclic Building Blocks-Thiazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2516-40-7,2-Bromobenzothiazole,as a common compound, the synthetic route is as follows.

General procedure: A 10 mL Schlenk tube equipped with a stir bar was sealed with a rubber septum,It was dried using a heat gun under reduced pressure (about 400 ¡ã C.)It was then filled with argon.Further, reduced pressure – argon filling was repeated twice to make the inside of the Schlenk tube completely under an argon atmosphere.0.5 mL of N, N’-dimethylpropyleneurea (hereinafter referred to as DMPU) as a solvent,0.71 mL of diethylzinc (1.02 M hexane solution: 1.5 eq),386.25 mg of nonafluorobutyl iodide (1.125 mmol, 2.25 eq) were sequentially added at room temperature using a syringe.Further, 0.5 mmol of 208.2 mg of dodecyl 2-iodobenzoate (0.5 mmol, 1 equivalent) as an electrophile,9.5 mg of copper iodide (0.05 mmol: 0.1 eq) was added,After replacing the rubber septum with a glass stopper, it was heated at 90 ¡ã C. for 16 hours.After allowing the reaction mixture to cool to room temperature, the reaction was stopped with 20 mL of 1 N hydrochloric acid,And extracted three times with diethyl ether having a total volume of 100 mL.The combined organic layer was washed with saturated brine,After drying with magnesium sulfate, the solvent was distilled off with a rotary evaporator.The crude product was purified by flash column chromatography (methylene chloride / hexane 1: 7)226.2 mg of the desired product was obtained (89percent, pale yellow oil)., 2516-40-7

2516-40-7 2-Bromobenzothiazole 612040, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; THE UNIVERSITY OF TOKYO; UCHIYAMA, MASANOBU; HIRANO, KEIICHI; (29 pag.)JP2015/86221; (2015); A;,
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13743-09-4, 2-Methyl-5-phenylthiazole-4-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 56:Compound 7: (2-methyl-5-phenylthiazol-4-yl)(5-((5-(trifluoromethyl)pyridin-2- ylamino)methyl)-6-azaspiror2.51octan-6-yl)methanoneIntermediate 9 (60 mg, 0.210mmol) ) was dissolved in dichloromethane (2ml), diisopropyl ethylamine (121 ul, 0.693mmol) and 0-(benzotriazol-1 -yl)-N,N,N’N’- tetramethyluronium hexafluorophosphate (1 12mg, 0.294mmol) were added. After 30 minutes at room temperature 2-methyl-5-phenylthiazole-4-carboxylic acid (65mg, 0.294mmol) was dissolved in dichloromethane (2ml) and dimethylformamide (1 ml) and added to the reaction. After 18 hours at room temperature the mixture was poured in aqueous NaHCO3 saturated solution and extracted with ethylacetate. The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; the obtained crude product was purified by silica gel column chromatography (gradient from dichloromethane/Ethyl acetate =1/1 to Ethyl acetate), thus obtaining 15 mg of compound 7 as white solid.MS (ESI) m/z 509 [M+Na]+. 1HNMR [the product is present as a mixture of conformers. The assignment refers to the major component] (CD3OD) d ppm 8.05 (s, 1 H) 7.39-7.60 (m, 5H) 6.41 (d, 1 H) 4.65 (m, 1 H) 4.20 (m, 1 H) 3.69-3.76 (m, 1 H) 3.28-3.35 (m, 1 H) 3.10-3.15(m, 1 H) 2.43 (s, 3H) 1.82 (m, 1 H) 1.30-1.45 (m, 1 H) 0.90-1.05 (m, 2H) 0.6-0.68 (m, 1 H) 0.30-0.55 (m, 2H) 0.15-0.25 (m, 2H).

13743-09-4, 13743-09-4 2-Methyl-5-phenylthiazole-4-carboxylic acid 943535, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; ROTTAPHARM S.P.A.; STASI, Luigi, Piero; ROVATI, Lucio; WO2011/6960; (2011); A1;,
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349-49-5, 4-(Trifluoromethyl)thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 3 2-Imino-3-methyl-4-trifluoromethyl-4-thiazoline fluorosulfonate 336 mg. of 2-amino-4-trifluoromethylthiazole was dissolved in 15 mg. CH2 Cl2. The flask was placed in an ice bath and 240 mg. of CH3 SO3 F in 5 ml. CH2 Cl2 was added. The mixture was then placed in a refrigerator over the weekend. The colorless crystals were collected on a filter to give 450 mg. (80percent) of 2-imino-3-methyl-4-trifluoromethyl-4-thiazoline fluorosulfonate, m.p. 177¡ã-178¡ã C., 349-49-5

The synthetic route of 349-49-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck & Co., Inc.; US4029803; (1977); A;,
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22900-83-0, Ethyl 2-bromo-4-methylthiazole-5-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Fluorophenol (Sigma-Aldrich; 2 g; 17.84 mmol), ethyl 2-bromo-4-methylthiazole-5- carboxylate (Ark Pharm; 4 g; 16 mmol), and cesium carbonate (Sigma-Aldrich; 6.24 g; 19.15 mmol) were thoroughly mixed in 32 ml anhydrous dimethylsulfoxide, and the resulting slurry stirred vigorously 16 h at 45¡ãC. After cooling to 25¡ãC, the reaction mixture was poured into 200 ml water. Organics were extracted with 4×100 ml ether, and the pooled extracts were washed with 50 ml water, washed with 50 ml brine, dried over anhydrous sodium sulfate, filtered, and concentrated to 4.51 g brown solid. NMR showed the desired product, ethyl 2- (4-fluorophenoxy)-4-methylthiazole-5-carboxylate, which was used in the next step without further purification. Yield: 4.51 g (100percent).1H NMR (400 MHz, CDCb): d 7.21 (m, 2H), 7.05 (m, 2H), 4.28 (q, 2H),) 2.48 (s, 3H), 1.32 (t, 3H, 22900-83-0

22900-83-0 Ethyl 2-bromo-4-methylthiazole-5-carboxylate 2824057, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; EBRIGHT, Richard H.; EBRIGHT, Yon W.; (72 pag.)WO2019/160873; (2019); A1;,
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13838-78-3, 5-Methylthiazole-2-carbaldehyde is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 3; 2-[[N-(5-Methyl-1 ,3-thiazol-2-yl)methylene]amino]-3-(1 ,3-thiazol-4-yl)propanoic acid, te/1-butyl ester A mixture of 2-amino-3-(1 ,3-thiazol-4-yl)propanoic acid, terf-butyl ester (Intermediate 2; 2.90 g, 12.7 mmol), 5-methyl-1 ,3-thiazole-2-carboxaldehyde (1.62 g, 12.7 mmol) and magnesium sulfate (ca. 1g) in dichloromethane (70 mL) was stirred at room temperature for 18 hours. The reaction mixture was filtered, and the filtrate was evaporated to remove solvent, to give the title compound as an oil.1H NMR (CDCI3): delta 8.75 (d, 1 H), 8.11 (s, 1 H), 7.55(br, 1 H), 7.02 (d, 1 H), 4.45 (dd, 1 H), 3.56 (dd, 1 H), 3.33 (dd, 1 H), 2.50 (br s, 3H) and 1.44 (s, 9H)., 13838-78-3

The synthetic route of 13838-78-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2006/45613; (2006); A1;,
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Thiazole | chemical compound | Britannica

61296-22-8,61296-22-8, 2-Amino-5-bromothiazole monohydrobromide is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Key Intermediate 1 Clnt-l A”) : 2-bromo-5-(3-ethoxy-benzesulfonylVthiazole [0103] Part A: A mixture of 3-ethoxythiophenol (10.0 g, 0.065 mol), 2-amino-5- bromothiazole monohydrobromide (17.7 g, 0.068 mol), 1 M aqueous NaOH (200 mL), and THF (200 mL) was stirred at RT for 15 min. The reaction mixture was warmed to 55 0C over Ih, cooled to RT and concentrated under reduced pressure to remove THF. The residue was partitioned between EtOAc (ca. 500 mL) and water (ca 100 mL), and the layers were separated. The organic phase was washed with saturated aqueous NaCl (1 x 200 mL), dried (Na2SO4), and concentrated under reduced pressure to give a solid. The solid was triturated with CH2Cl2.”hexanes (ca. 10:1) to provide 5-(3-ethoxy-phenylsulfanyl)-thiazol-2-ylamine (13.2 g, 80%) as a light brown solid. LCMS (m/z): 253 (M+H)+

As the paragraph descriping shows that 61296-22-8 is playing an increasingly important role.

Reference£º
Patent; ICAGEN, INC.; WO2007/75852; (2007); A2;,
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Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1452-16-0,2-Cyanothiazole,as a common compound, the synthetic route is as follows.

A mixture of 5 mg iron trichloride (FeCI3), 2 g of sodium and 40 ml of t-amylalcohol is heated to 110 0C for 20 minutes before a mixture of 3.9 g of the thiazole-2-nitrile of the formula 1 and 7.82 g of 8 is added portion-wise. The reaction mixture is stirred at 1 10 0C for 3 hours before it is poured onto 6.3 g acetic acid in a water-methanol mixture (100ml/100ml). Bchner filtration and exhaustive washing with methanol affords 4.5 g of the desired 1 ,4- diketopyrrolo[3,4-c]pyrrole (DPP) derivative of the formula A-42 as dark blue powder; ESI- MS m/z (% int.): 302.15 ([M+H]+, 100%)., 1452-16-0

1452-16-0 2-Cyanothiazole 15111480, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; BASF SE; HAYOZ, Pascal; AEBISCHER, Olivier Frederic; DUeGGELI, Mathias; TURBIEZ, Mathieu G. R.; FONRODONA TURON, Marta; CHEBOTAREVA, Natalia; WO2010/115767; (2010); A1;,
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20949-81-9, 2-Phenylthiazole-4-carbaldehyde is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

20949-81-9, COMPOUND 12.1. 38: 4-{6,7-DIMETHOXY-2-[(2-PHENYL-1,3-THIAZOL-5- YL) METHYLl-1, 2, 3, 4-TETRAHYDROISOOUINOLIN-1-YL- N- DIETHYLBENZAMIDE; INTERMEDIATE 5.1. 7 (50 mg, 0.14 mmol) and 2-phenyl-4-thiazolecarbaldehyde (51 mg, 0.27 mmol) were dissolved in 1,2-dichloroethane (2 mL) and sodium triacetoxyborohydride (115 mg, 0.54 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. Resin-bound tosylhydrazine (0.27 g, 1.5 mmol/g) was added and the mixture was agitated for another 2 h. Dichloromethane and 2 M aqueous sodium hydroxide solution were added, the mixture was shaken and passed through a Whatman 1PS filter paper. The organic phase was evaporated to dryness and purified by flash chromatography to yield the product (74 mg, 0.136 mmol, quant.). 1H NMR (500 MHz, CDC13) : 1.09, 1.23 (2 brs, 6H), 2.80, 3.04, 3.28 (3 m, 6H), 3.52 (brs, 2H), 3.82, 3.90 (2 d, J 14 Hz, 2H), 3.61, 3.85 (2 s, 6H), 4.78 (s, 1H), 6.20, 6.63 (2 s, 2H), 7.35-7. 43 (m, 7H), 7.94 (d, J 7.5 Hz, 2H). (+) LRESIMS m/z 542 (100) [M+H] +.

The synthetic route of 20949-81-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
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Thiazole | chemical compound | Britannica

6436-59-5, Ethyl 2-methylthiazole-4-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 46 Ethyl 2-methyl-1 ,3-thiazole-4-carboxylate [6436-59-5] (5.0g, 29.2mmol) was dissolved in acetonitrile (50ml_). To this, NBS (5.7g, 32.03mmol) was added at room temperature and the mixture heated at reflux for 2 hours. To this, NBS (2.5g, 14.05mmol) was added and the mixture heated at reflux for 2 hours. To this, NBS (2.5g, 14.05mmol) was added and the mixture heated at reflux for 18 hours. The mixture was diluted with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was dried with MgS04, filtered and concentrated in vacuo to dryness. The residue was purified by chromatography on silica eluting with 0-50% ethyl acetate/cyclohexane. The fractions containing the desired product were combined and the solvents removed by evaporation in vacuo to give Intermediate 46 (1.58g) as a cream solid. LCMS (Method 2) Rt 2.88 min; m/z(M+H)+ 250/252, 6436-59-5

As the paragraph descriping shows that 6436-59-5 is playing an increasingly important role.

Reference£º
Patent; ANTABIO SAS; LEMONNIER, Marc; DAVIES, David; PALLIN, David; WO2014/198849; (2014); A1;,
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Thiazole | chemical compound | Britannica

74370-93-7, 4-(tert-Butyl)thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-(iert-butyl)thiazol-2-amine (200 mg, 1.28 mmol), and DIEA (438 muIota_, 2.56 mmol) in THF (1.5 mL) was added cyclopentanecarbonyl chloride (172 muL, 1.41 mmol). After allowing to stand at ambient temperature for 1 h, the mixture was washed with 1 N NaOH (2X2 mL), brine (2X2 mL), dried with sodium sulfate, filtered, and concentrated. Flash chromatography (0-20% hexanes/ethyl acetate) provided N-(4-tert-butyl-1 ,3-thiazol-2- yl)cyclopentanecarboxamide (286 mg, 89% yield) (A127) as a colorless solid. LCMS for C13H2oN2OS, found 253 [M+H]+., 74370-93-7

74370-93-7 4-(tert-Butyl)thiazol-2-amine 2734202, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; KEZAR LIFE SCIENCES; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; MCMINN, Dustin; JOHNSON, Henry; TAUNTON, John, William; CARRASCO, Yazmin, Paulina; SHARP, Phillip, Patrick; (156 pag.)WO2019/46668; (2019); A1;,
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Thiazole | chemical compound | Britannica