Day: March 16, 2022

14542-13-3, 2-Methoxythiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 2-methoxythiazole ( 5 g, 43.4 mmol) in tetrahydrofuran(THF) (50 mL) was added n-BuLi (35.3 mL, 56.4 mmol) and the contents stirred at -78 C.After 15 min, tributylchlorostannane (14.13 mL, 52.1 mmol) was added and the mixturestirred with warming to room temperature over a 3 h period. The reaction mixture wasquenched with water (20 mL) and the contents extracted with ether (25 mL ). The organic layer was separated and dried over anhydrous sodium sulphate, filtered, and the filtrateconcentrated in vacuo to afford the crude product (6 g). The crude product was purified bysilica gel column chromatography (eluent: 2% EtOAc/Hexane) to afford 2-methoxy-5-(tributylstannyl)thiazole (4 g, 22%) as yellow liquid. 1H NMR (400 MHz, CDCl3-d3) 8ppm 0.90-0.98 (m, 9H), 1.05-1.15 (m, 6H),1.30-1.40 (m, 6H), 1.50-1.65 (m, 6H), 4.04 (s, 3H), 7.03 (s, 1H). LCMS(ES) [M+Ht 405.99., 14542-13-3

14542-13-3 2-Methoxythiazole 575451, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; GLAXOSMITHKLINE LLC; BURGESS, Joelle, Lorraine; DUQUENNE, Celine; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; VERMA, Sharad, Kumar; WO2013/173441; (2013); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

167366-05-4, 4-Bromo-2-formylthiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a rb flask with an attached Dean-Stark trap containing molecular sieves, 4A (0.25g) was added 4-bromothiazole-2-carbaldehyde (4.4 g, 22.91 mmol). The starting material was dissolved in Benzene (45 ml) and Ethylene glycol (1.406 ml, 25.2 mmol) was added followed by pTsOH (0.218 g, 1.146 mmol). The mixture was heated to reflux for 3 h. The mixture was cooled to rt, and was partitioned with sat. aq. NaHCO3. The mixture was washed 2* with sat. NaHCO3 (40 mL), then once with sat. NaCl (40 mL). The organic layer was dried with Na2SO4. The drying agent was removed by filtration, and the mixture was concentrated under reduced pressure. The residue was purified by biotage flash chromatography using a 40+M column and a 0 to 20% EtOAc in hexanes gradient. The product, 4-bromo-2-(1,3-dioxolan-2-yl)thiazole (5.1 g, 21.60 mmol, 94% yield), was collected as a light-yellow oil. To a solution of 4-bromo-2-(1,3-dioxolan-2-yl)thiazole (5.09 g, 21.56 mmol) in Toluene (100 ml) was added Hexamethylditin (10 g, 30.5 mmol) followed by Tetrakis (2.491 g, 2.156 mmol). The mixture was attached to a reflux condenser, and was flushed with N2. The mixture was heated to 100 C. for 4 h. The mixture was cooled to rt, and was loaded onto a 40+M biotage cartridge that was pre-saturated with hexanes with 0.1% Et3N. The desired product was purified using a 0-20% EtOAc in hexanes with 0.1% Et3N gradient. After concentrating in vacuo, the product, 2-(1,3-dioxolan-2-yl)-4-(trimethylstannyl)thiazole (4.64 g, 14.50 mmol, 67.3% yield), was isolated as a light-yellow oil. LCMS: m/e 322.0 (M+H)+, ret time 2.23 min (method 7); 1H NMR (500 MHz, CDCl3) delta ppm 7.39 (s, 1H) 6.20 (s, 1H) 4.03-4.20 (m, 4H) 0.27-0.42 (m, 9H)., 167366-05-4

As the paragraph descriping shows that 167366-05-4 is playing an increasingly important role.

Reference：
Patent; Bristol-Myers Squibb Company; US2007/249579; (2007); 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.3034-53-5,2-Bromothiazole,as a common compound, the synthetic route is as follows.

0.15mol containing a solution of 2-bromothiazole added dropwise to a solution containing 0.18mol butyllithium was added dropwise for about 2h, after the addition was completed, stirring was continued for 1h, maintained at low temperature (-78 deg.] C) reaction carried out under . 0.3mol ethyl acetate and then added to the solution dropwise addition was completed, stirring was continued for 3h, the reaction is complete, the organic phase extracted was allowed to stand, washed with distilled water, dried over anhydrous Na2SO4 was added, and then distilled under reduced pressure collecting bp89 ~ 91 / 1.6kPa fraction, 2-acetyl thiazole 18.16g. The yield was 95.2%., 3034-53-5

3034-53-5 2-Bromothiazole 76430, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Wutong Aroma Chemicals Co. Ltd.; Li, Xin; Sun, Bin; Wei, Jie; Wang, Xiaodong; Zhao, Leizhen; Zang, Chuanjin; Zi, Yanyan; Liu, Yuanwu; Gao, Ming; (8 pag.)CN105348216; (2016); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

5198-79-8, 2-Chloro-4-formylthiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A solution of 2,3-diamino-1,4-naphthoquinone (1.0 mmol),appropriate aromatic aldehyde (1.0 mmol) with sodium pyrosulfitein DMF was stirred at 120 C overnight. On completion of the reactionmonitored by TLC, the solvent was evaporated and the residuewas purified by silica gel chromatography by DCM/MeOHsystem to afford the final product. If necessary, the crude productcould be recrystallized in methanol or DMSO to afford pure sample.4.1.5.1. 2-(2-Chlorophenyl)-1H-naphtho[2,3-d]imidazole-4,9-dione(T1). Pale yellow solid; yield 80%;, 5198-79-8

As the paragraph descriping shows that 5198-79-8 is playing an increasingly important role.

Reference：
Article; Pan, Liangkun; Zheng, Qiang; Chen, Yu; Yang, Rui; Yang, Yanyan; Li, Zhongjun; Meng, Xiangbao; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 423 – 436;,
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.14527-44-7,Methyl thiazole-5-carboxylate,as a common compound, the synthetic route is as follows.

Step 1: Sodium 2-cyano-1-(1,3-thiazol-5-yl)ethenolate A solution of 1.5 g (10.5 mmol) of methyl 1,3-thiazole-5-carboxylate and 430 mg (10.8 mmol) of acetonitrile in 15 ml of THF was added dropwise to a suspension of 419 mg of sodium hydride (60% strength suspension in mineral oil) in 16 ml of THF which was heated under reflux. The reaction mixture was heated under reflux for 20 h. After cooling, 50 ml of methyl tert-butyl ether were added and the mixture was stirred for 30 minutes. The resulting precipitate was filtered off with suction through a frit and dried under oil pump vacuum. This gave 1.71 g (94% of theory) of the title compound which was combined with the product (3.48 g, 95% of theory) from a second batch starting with 3.0 g (21 mmol) of methyl 1,3-thiazole-5-carboxylate.

14527-44-7, As the paragraph descriping shows that 14527-44-7 is playing an increasingly important role.

Reference：
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SUessMEIER, Frank; LOBELL, Mario; GRUeNEWALD, Sylvia; HAeRTER, Michael; BUCHMANN, Bernd; TELSER, Joachim; JOeRIssEN, Hannah; HEROULT, Melanie; KAHNERT, Antje; LUSTIG, Klemens; LINDNER, Niels; US2013/190290; (2013); 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.182344-56-5,2-Chloro-4-fluorobenzo[d]thiazole,as a common compound, the synthetic route is as follows.

General procedure: GP4-1: A mixture of substituted2-chlorobenzothiazole (1.0eq), N-Bocpiperazine (1.05 eq) and Na2CO3 (1.2 eq) inDMF (10 volume) was heated up at 100 0C for hours, the process ofwhich was monitored by TLC. The mixture was diluted by EA and added by water.After extraction by EA (2 times), the collected organic layers were washed by10% citric acid, and then brine, dried over Na2SO4 andconcentrated to give crude product, which could be used directly withoutfurther purification.GP4-2: N-Bocprotected amine in DCM (5 volume) was added by TFA (2.5 volume). The mixturewas stirred at rt for four hours and monitored by TLC. After consumption ofstarting material, volatile solvent was removed under reduced pressure and theresidue was neutralized by saturated Na2CO3 solution toobtain the slurry, which was extracted by 10% methanol in DCM (3 times). Theorganic layers were collected, dried and concentrated to give the desired freeamine, for direct use for next step.GP4-3: Free amine (1.0 eq) suspendedin DCM (10 volume) was added by aldehyde (1.1 eq) under N2atmosphere. The mixture was stirred at rt 15 min. Then trimethylsilylazide (TMSN3, 1.1 eq) was added, and stirring was kept foranother 15 min, followed by addition of isonitrile (1.0 eq). The mixture wasstirred at for 12 h. After removal of solvent, the residue was purified bypreparative TLC (DCM/MeOH as eluent) to give the product, which could bere-purified by trituration with ether., 182344-56-5

As the paragraph descriping shows that 182344-56-5 is playing an increasingly important role.

Reference：
Article; Lv, Fengping; Li, Zhi-Fang; Hu, Wenhao; Wu, Xiaohua; Bioorganic and Medicinal Chemistry; vol. 23; 24; (2015); p. 7661 – 7670;,
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.40283-41-8,2-Aminothiazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of (+/-)-cis-N1-(2-chloro-7-methyl-7H-pyrrolo[2,3 -d]pyrimidin-4-yl)cyclohexane-1,3-diamine ( 62 mg, 0.22 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) was added N,N-diisopropylethylamine (0.11 mL, 0.66 mmol) and 2-aminothiazole-4-carboxylic acid (63 mg, 0.44 mmol). The mixture was stirred at rt for 10 minitues, and then HATU (168 mg, 0.44 mmol) was added. The resulting mixture was stirred at rt for 3 h. To the reaction mixture was added water (10 mL), and the resulting mixture was extracted with ethyl acetate (10 mL x 3). The combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give the title compound as a colorless solid (89.9 mg, 100%).MS (ESI, pos.ion) m/z: 406.5[M+H].

40283-41-8, 40283-41-8 2-Aminothiazole-4-carboxylic acid 1501882, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); 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.15864-32-1,2-Amino-6-bromobenzothiazole,as a common compound, the synthetic route is as follows.

Step 3) Formation of6-(4,4,5,delta-tetramethyl-1,3-dioxaborolan-2-yl)-1,3-henzoi.azol-2- amineTo a solution of 6-bromo~1 ,3-benzothiazoi-2~amine (10 g, 43.6 mmoi) in dioxane (50 mL) was added bispinacoiotodiboron (16.6 g, 65.4 mmol), potassium acetate (12.8 g, 130.8 mmol) and PdCI2dppf.DCM (3.55 g, 43.6 mmol) and the resulting mixture was stirred at 100&;C for 12 h. After cooiing to RT the reaction mixture was filtered through a plug of Celite which was further washed with EA. The combined filtrate was evaporated to dryness and the residue purified by column chromatography (PBEA1 85/15) to afford the title compound (5.1 g, 42%) as a white solid. 1H NMR (DMSO-dt, 400 MHz) delta 7.92 (s, 1 H)1 7.65 (bs, 2H)1 7.50 (d, J= 8.7 Hz1 1 H)1 7.29 (d, J = 8.2 Hz,1 H), 1.27 (s, 12H)., 15864-32-1

15864-32-1 2-Amino-6-bromobenzothiazole 85149, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; MERCK SERONO S.A.; SWINNEN, Dominique; JORAND-LEBRUN, Catherine; GRIPPI-VALLOTTON, Tania; GERBER, Patrick; GONZALEZ, Jerome; SHAW, Jeffrey; JEYAPRAKASHNARAYANAN, Seenisamy; WO2010/100144; (2010); 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.14527-43-6,Ethyl thiazole-4-carboxylate,as a common compound, the synthetic route is as follows.

Methyl Iodide (140?mL, 2.25?mol, 5.0 equiv) was dissolved in Et2O (450?mL) and added dropwise to Mg turnings (54.3?g, 2.25?mol, 5.0 equiv) under a constant flow of nitrogen. When all magnesium dissolves ester 13 (70.24?g, 447?mmol) in Et2O (450?mL) was added dropwise. The reaction mixture was left overnight and resulted suspension was carefully (very exothermic + gas evolution.) was poured into saturated aqueous NH4Cl (~2?L). The resulted solution was extracted with Et2O (3?*?200?mL). The combined organic layers were dried over Na2SO4 and evaporated to give the pure compound. M?=?48.26?g. Yield?=?75%. 1H NMR: (CDCl3, 400?MHz) delta?=?1.61 (s, 6?H), 3.27 (br. s, 1?H), 7.17 (d, J?=?2.0?Hz, 1?H), 8.73 (d, J?=?1.8?Hz, 1?H). 13C NMR: (CDCl3, 100?MHz) delta?=?30.2 (2C), 71.2, 77.2, 111.6, 152.9, 165.0., 14527-43-6

The synthetic route of 14527-43-6 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Curreli, Francesca; Belov, Dmitry S.; Kwon, Young Do; Ramesh, Ranjith; Furimsky, Anna M.; O’Loughlin, Kathleen; Byrge, Patricia C.; Iyer, Lalitha V.; Mirsalis, Jon C.; Kurkin, Alexander V.; Altieri, Andrea; Debnath, Asim K.; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 367 – 391;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

824403-26-1, 5-Bromo-2-chlorobenzo[d]thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

824403-26-1, A stirred mixture of 2-chloro-5-bromobenzothiazole (CAS No.824403-26-1, catalog No.20284, Daxian Chemical Institute Ltd., No.179, 10169 New Hampshire Ave., Silver Spring, Md. 20903, 2.485 g, 0.0100 mole), (R)-1-(pyrrolidin-3-yl)piperidine dihydrochloride (Reference Example 5c, 2.73 g, 0.0120 mole), and potassium carbonate (6.00 g, 0.04438 mole) in N,N-dimethylformamide (15 mL) is heated to 100 C. with an oil bath for 15 hours. The reaction mixture is cooled to room temperature then poured into water (300 mL). The resulting precipitate is collected by filtration and the filter cake is rinsed with water (600 mL). The solid is dissolved in dichloromethane and the solution is dried (MgSO4) and filtered. The filtrate is concentrated under reduced pressure to give a solid that is crystallized from hot ethyl acetate to give (R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole.

As the paragraph descriping shows that 824403-26-1 is playing an increasingly important role.

Reference：
Patent; Abbott Laboratories; US2009/163464; (2009); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica