Category: thiazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3622-35-3,Benzo[d]thiazole-6-carboxylic acid,as a common compound, the synthetic route is as follows.

Under nitrogen atmosphere at -78 C, 11BuLi/Hex(2.5M) (28.5 mL, 71.4 mmol) was added dropwise into the solution of 6-carboxybenzothiazole (6.566 g, 37 mmol) in THF (450 mL) over 25 minutes. After the mixture was stirred for additional half an hour, the solution of Boc-HN-Arg(Mtr) Weinreb amide (1.633 g, 3.08 mmol) in THF (60 mL) was added slowly over 20 mm at -78C. After the addition then the mixture was stirred at -24 C to -20 C for 1.5 hours. The reaction was quenched with saturated aqueous NH4C1 (270 mL). The layers were separated and the aqueous layer was extracted with AcOEt. The organic phase was collected and washed with water and brine, dried with Na2SO4 then concentrated in vacuo. To the resulting residue MeOH (50 mL) was added. The mixture was cooled at -25 C and sodium borohydride (0.706 g, 18.7 mmol) was added. The mixture was stirred at -25 -20 C for 1 hour. Acetone (10 mL) was added to quench the reaction and the mixture was stirred for 15 minutes then concentrated in vacuo. The residue was suspended in water, acidified to pH 34, and extracted with AcOEt. The organic phase was washed with brine, dried with Na2SO4, then concentrated in vacuo. The resulting residue was dissolved in CH2C12/MeOH (17/3 v/v, 40 mL), cooled to 0 C. Into it, (trimethylsilyl)diazomethane (2 M in hexane, 9.2 mL, 18.4 mmol) was added dropwise over 25 minutes. The mixture was stirred at 0 C for ihour. MeOH (5 mL) was added and the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography with CHC13/MeOH combination as eluent to give BocHN-Arg(Mtr)-CH(OH)benzothiazole-6-COOMe a (0.445 g, mixture of diastereomers) in 22% yield. MS(ESI): found: [M + Hj, 664.5., 3622-35-3

3622-35-3 Benzo[d]thiazole-6-carboxylic acid 601670, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; WASHINGTON UNIVERSITY; JANETKA, James,, W.; HAN, Zhenfu; HARRIS, Peter; KARMAKAR, Partha; (163 pag.)WO2016/144654; (2016); A1;,
Thiazole | C3H3NS – PubChem
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42270-37-1, 2-(Piperazin-1-yl)thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,42270-37-1

Hinokitiol (0.29 g, 1.8 mmol), 1-(2-thiazolyl) piperazine (0.30 g, 1.8 mmol) and acetic acid (0.1 mL, 1.8 mmol) were mixed with 10 mL of methanol and then 37% aqueous formalin (0.16 mL, 18 mmol) was added. After stirring at room temperature overnight, 2-hydroxy-4-isopropyl-7-[4-(2-thiazolyl)piperazinomethyl]-2,4,6-cycloheptatrien-1-one (0.3 g, 0.87 mmol, 49%) was obtained by collecting the formed crystals by filtration.

42270-37-1 2-(Piperazin-1-yl)thiazole 911806, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Nippon Kayaku Kabushiki Kaisha; EP1504759; (2005); A1;,
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288-47-1, Thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of 4-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-thia-3,3b,5-triaza-cyclopenta[a]pentalen-5-yl]-butyric acid ethyl ester (Compound 37) As depicted in Scheme 24 below, anhydrous Co(OAc)2 (0.021 mmol, 5%) and SALEN (2,2′-(1,4-diiminobutane-1,4-diyl)diphenol, 0.041 mmol, 0.1 molequivalent) in 0.5 ml dry dioxane are placed in a flame-dried flask, and the mixture is stirred for 10 minutes at room temperature. A solution of thiazole (0.411 mmol) in 1 ml dry dioxane, anhydrous Cs2CO3 (0.493 mmol, 1.2 molequivalents) and CuI (0.822 mmol, 2 molequivalents) are thereafter added consecutively to the reaction mixture under argon. A solution of 4-nitrophenyl iodide (0.493 mmol, 1.2 molequivalents) in dry dioxane (0.5 ml) is then added dropwise and the resulting mixture is heated to 150 C. under argon, while monitoring the reaction progress by TLC. Once the reaction is completed (after about 10 hours), the resulting mixture is diluted with chloroform (20 ml) and filtered through a celite pad. The organic solvents are evaporated under reduced pressure and the crude product is purified by flash column chromatography, using a hexane:ethyl acetate mixture as eluent, to give pure 2-[4-nitrophenyl]thiazole.

288-47-1, The synthetic route of 288-47-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Gelder, Joel M. Van; Klein, Joseph Y.; Basel, Yochai; Reizelman, Anat; Tchilibon, Susanna; Mouallem, Orly; US2008/39456; (2008); A1;,
Thiazole | C3H3NS – PubChem
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101080-15-3, 5-Isopropylthiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The thiazole amine (69 mmol) was combined with 2- (S)-tert-butoxycarbonylamino- pentanoic acid (69 mmol) in 170 mL of anhydrous DMF under N2. Triethylamine (76 mmol) was added to the reaction, followed by HOBT (76 mmol) and EDCI (76 mmol). The resultant mixture was stirred at r. t. for 16h. The reaction was then diluted with 200 mL of EtOAc and washed with 200 mL of water and brine. The organics were then dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product, [1-(5-Isopropyl-thiazol- 2-ylcarbamoyl)-butyl]-carbamic acid ter-butyl ester. The product (10.2 mmol) was purified through flash chromatography and dissolved in 15 mL of anhydrous 4.0 N HCI in dioxane and stirred at rt for 2 h. The reaction was then concentrated under reduced pressure and triturated in Et20 to give the desired amine, 2- Amino-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide, 101080-15-3

The synthetic route of 101080-15-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER PRODUCTS INC.; WO2005/95367; (2005); A1;,
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14527-44-7, Methyl thiazole-5-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-(5-(4-Methoxybenzyloxy) pyridin-2-yl)thiazole-5-carboxylate A mixture of 2-bromo-5-(4-methoxybenzyloxy)pyridine (1.10 g), methyl thiazole-5-carboxylate (644 mg), Pd(P(t-Bu)3)2 (153 mg), Cs2CO3 (1.20 g) and DMF (10 mL) was evacuated and refilled with nitrogen three times. The mixture was stirred at 150 C. under N2 atmosphere for 3 hours. Insoluble material was removed by filtration through Celite. The filtrate was diluted with H2O (100 mL). The solid obtained was collected by filtration and washed with MeOH to provide the subtitle compound. MS ESI+: m/z=357 [M+H]+., 14527-44-7

The synthetic route of 14527-44-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SANOFI; SCHWINK, Lothar; BOSSART, Martin; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; KLABUNDE, Thomas; MAIER, Thomas; STENGELIN, Siegfried; US2014/99333; (2014); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3622-35-3,Benzo[d]thiazole-6-carboxylic acid,as a common compound, the synthetic route is as follows.

A solution of benzothiazole-6-carboxylic acid (4.48 g, 25.0 mmol), tert-butyl carbazate (3.63 g, 27.5 mmol), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (5.75 g, 30.0 mmol) and 1-hydroxybenzotriazole (4.05 g, 30.0 mmol) in N,N-dimethylformamide (50 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/tetrahydrofuran=2/1), and crystallized from hexane/acetone to give the title compound (5.51 g, yield 75%) as colorless crystals. melting point 128-129 C.1NMR (CDCl3) delta 1.52 (9H, s), 6.81 (1H, brs), 7.89 (1H, dd, J=1.7, 8.7 Hz), 8.12 (1H, d, J=8.7 Hz), 8.40 (1H, brs), 8.47 (1H, dd, J=0.6, 1.7 Hz), 9.12 (1H, s).Elemental analysis (for C13H15N3O3S)Calculated (%): C, 53.23; H, 5.15; N, 14.32.Found (%): C, 53.10; H, 5.13; N, 14.38., 3622-35-3

The synthetic route of 3622-35-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Itoh, Fumio; US2010/69381; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

939-69-5, 6-Hydroxybenzo[d]thiazole-2-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

939-69-5, Method A: Preparation of a 5-Oxymethyl-D-Luciferin Cycloheximide Conjugate [00190] 5-Hydroxymethyl-D-Luciferin. A modification of the procedure of Seto, S., et al., 1963 is used. A mixture of 2-Cyano-6-hydroxybenzthiazole (200 mg), ?-hydroxymethyl D-Cysteine (200 mg), potassium carbonate (160 mg) and 50% aqueous methanol (10 mL) is stirred under a stream of nitrogen gas, at room temperature for 2.5 hours. After neutralization with 1 N aqueous HCl, the precipitate is collected, washed with water and recrystallized from 95% ethanol to give the title compound. [00191] 6′-O-t-butyldimethylsilyl-5-hydroxymethyl-D-Luciferin, t-butyldimethylsilyl ester. Under anhydrous conditions. 5-hydroxymethyl-D-Luciferin (45mg, 0.145 mmole) is dissolved in anhydrous dimethylformamide (7 mL), cooled to 0 C. (ice-bath) and imidazole (300 muL) and t-butyldimethylsilyl chloride solution (50% solution in tetrahydrofuran, 52 muL, 2.1 equiv.) is added. The reaction mixture is allowed to stir at 0 C. for 2 hours and at room temperature overnight. The major product is purified by silicagel column chromatography using dichloromethane:ethylacetate gradient elution. Fractions containing the first major product to elute from the column are combined and evaporated to give the title compound as a white solid.

939-69-5 6-Hydroxybenzo[d]thiazole-2-carbonitrile 9881912, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Marker Gene Technologies, Inc.; US6656917; (2003); B1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3034-53-5,2-Bromothiazole,as a common compound, the synthetic route is as follows.

Example 4 1-phenyl-8-[[2-(2-thiazolyl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one (Compound 24) Step A: To a mixture of 2-bromothiazole (826 mg, 4.99 mmol) and tetrakis(triphenylphosphine) palladium (0) (175 mg, 0.151 mmol) in 1,2-dimethoxyethane (20 mL) was added 2-formylbenzeneboronic acid (0.9017 g, 6.01 mmol) and 1 N aqueous NaHCO3 (8 mL). The resultant mixture was heated at reflux for 6 hrs. The reaction mixture was diluted with water and extracted with EtOAc (2 X 50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was purified by gradient flash chromatography (10% to 25% EtOAc in hexane) to yield 2-(2-thiazolyl)benzaldehyde as a white solid. MS (loop pos) MH+ = 190.1 1 H NMR (300 MHz, CDCl3) 7.50 (m, 1 H), 7.55-7.60 (m, 1 H), 7.65-7.70 (m, 1 H), 7.75-7.80 (m, 1 H), 7.95-7.97 (m, 1 H), 8.00-8.05 (m, 1 H), 10.5 (s, 1 H)

3034-53-5, The synthetic route of 3034-53-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Janssen Pharmaceuticals, Inc.; JORDAN, Alfonzo; PAN, Kevin; REITZ, Allen, B.; (71 pag.)EP1392687; (2017); B1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15864-32-1,2-Amino-6-bromobenzothiazole,as a common compound, the synthetic route is as follows.

To a stirred solution of 6-bromobenzo[d]thiazol-2-amine I-2 (229 g, 1.0 mol), pyridine (237 g, 3.0 mol) and DMAP (1.0 g) in anhydrous THF (1800 mL) at 10 C., CH3COCl (87 g, 1.1 mol) was added dropwise and the temperature was kept below 20 C. The resulting mixture was allowed to warm to RT and stirred overnight. The mixture was poured into H2O (2000 mL) and extracted with ethyl acetate (2000 mL). The organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was suspended in chloroform (1200 mL), heated to reflux for 20 min. and then cooled to RT. The precipitate was collected by filtration and further dried in vacuo to afford the desired product, N-(6-bromobenzo[d]thiazol-2-yl) acetamide (I-3) (231 g, 85% yield) as a white solid. ESI-MS (M+H)+ m/z: 270.95, 15864-32-1

As the paragraph descriping shows that 15864-32-1 is playing an increasingly important role.

Reference：
Patent; Intellikine LLC; Ren, Pingda; Liu, Yi; Wilson, Troy Edward; Li, Liansheng; Chan, Katrina; US2015/225407; (2015); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3622-38-6,2-Chloro-5-nitrobenzo[d]thiazole,as a common compound, the synthetic route is as follows.

Step: 100 mg, 0.67 mmol of benzo[c][1,2]oxaborol-1,5(3H)-diol was dissolved in 8 mL of acetonitrile.Then, 172 mg, 0.8 mmol of 2-chloro-5-nitrobenzothiazole and 329.1 mg, 1.01 mmol of cesium carbonate were added, and the mixture was stirred at 50 ° C overnight, cooled to room temperature, then added with water, and the solid was precipitated, and the crude product solid was prepared. Purification by phase separation to give 5-(5-nitrobenzothiazol-2-oxy)benzo[c][1,2]oxaborol-1(3H)-ol as a white solid 15 mg. The yield was 6.8percent., 3622-38-6

The synthetic route of 3622-38-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Guangzhou Baiting Pharmaceutical Technology Co., Ltd.; Wu Zhong; Li Jingrong; (16 pag.)CN108997394; (2018); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica