Heterocyclic Building Blocks-Thiazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32137-76-1,Ethyl 1,3-benzothiazole-2-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of A (10 g, 48 mmol) in THF (50 mL) at 0C under nitrogen was added aq.NaOH (72ml, 2M, 145 mmol). Reaction mixture was stirred at room temperature for 30-120min, monitored by TLC. Mixture was acidified with aq.HCl (6M) to pH=3-4, and precipitate filtered to give 1 (7 g, 81%) as a white solid., 32137-76-1

32137-76-1 Ethyl 1,3-benzothiazole-2-carboxylate 640708, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; THE CALIFORNIA INSTITUTE FOR BIOMEDICAL RESEARCH; THE SCRIPPS RESEARCH INSTITUTE; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; CHATTERJEE, Arnab, K.; WANG, Feng; SCHULTZ, Peter, G.; XU, Chunping; AJAYI, Kehinde; WANG, Jianing; HALDER, Rajkumar; KUMAR, Puneet; YANG, Baiyuan; LIU, Renhe; CHENG, Bo; KANEKO, Takushi; WO2014/190199; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61830-21-5,Ethyl 2-amino-5-bromothiazole-4-carboxylate,as a common compound, the synthetic route is as follows.,61830-21-5

General procedure: A mixture of 2-amino-5-bromothiazole-4-carboxylate (34, 2.22g,0.01 mol), the appropriate 2-thioxo-quinazoline analogs (14-17,0.01 mol), anhydrous potassium carbonate (1.5 g, 0.01 mol) in DMF(10 ml) was heated under reflux for 14-16 h. Solvent was then removed under reduced pressure and continued as mentioned under compounds 21-24 (Table 1).

The synthetic route of 61830-21-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Al-Omary, Fatmah A.M.; Hassan, Ghada S.; El-Messery, Shahenda M.; Nagi, Mahmoud N.; Habib, El-Sayed E.; El-Subbagh, Hussein I.; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 33 – 45;,
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3704-41-4, 2-(4-Nitrophenyl)thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-(4-nitrophenyl)thiazole (6 g, 29.10 mmol, 1 eq.) in DMF (50 mL), was added NBS (15.54 g, 87.29 mmol, 3 eq.). The mixture was stirred at 80C for 15 mins and LCMS showed the reaction was complete. The mixture was poured into water (1L) and filtered. The filter cake was washed with MeOH (50 mL) and dried to give 5-bromo-2- (4- nitrophenyl)thiazole (7.3 g, crude) as a yellow solid. 1H NMR (400MHz, METHANOL-d4) delta = 8.35 (br s, 2H), 8.18 (br s, 2H), 8.07 – 7.88 (m, 1H).

3704-41-4, 3704-41-4 2-(4-Nitrophenyl)thiazole 13546655, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; CYTEIR THERAPEUTICS, INC.; CASTRO, Alfredo, C.; MCCOMAS, Casey, Cameron; VACCA, Joseph; (214 pag.)WO2019/14315; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7336-54-1,N-(5-bromothiazol-2-yl)acetamide,as a common compound, the synthetic route is as follows.,7336-54-1

EXAMPLE 79 A mixture of 2-acetylamino-5-bromothiazole (2.2 g), 4-amino-2-mercaptopyrimidine (1.3 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (50 ml) was heated at 90 C. for 2 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The precipitation was collected by filtration, washed with water and dried in vacuo to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 200 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-acetylamino-5-(4-aminopyrimidin-2-ylthio)thiazole (1.3 g, yield: 48.7%). mp: 255-258 C. (dec.) IR (Nujol): 3400, 3350, 3200, 1692, 1650, 1585, 1325, 1300 cm-1 NMR (DMSO-d6, 200 MHZ, ppm): 2.16 (3H, s), 6.17 (1H, d, J=6Hz), 7.02 (2H, s), 7.59 (1H, s), 7.85 (1H, d, J=6Hz), 12.31 (1H, s) Mass: M+1 268, M 267, m/e 225, 205, 183

As the paragraph descriping shows that 7336-54-1 is playing an increasingly important role.

Reference£º
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5256675; (1993); A;,
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137-00-8, 4-Methyl-5-thiazoleethanol is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-(2-hydroxyethyl)-4-methylthiazole 7 (3.0 g, 21.0 mmol) and methyl iodide (2.64 mL, 42.0 mmol) were mixed and refluxed for 2 h. After evaporation of excess methyl iodide, to the residual brown syrup was added ether (50 mL) and stirred for 30 min, the precipitate was filtered to get 17 as a pale-yellow solid (5.76 g, 96.3%). Mp: 82-84 C; 1H NMR (D2O, ppm): 4.14 (s, 3 H, CH3N), 3.90 (t, 2 H, CH2CH2O, J = 5.6 Hz), 3.19 (t, 2 H, CH2CH2O, J = 6.0 Hz), 2.53 (s, 3 H, CCH3).

137-00-8, The synthetic route of 137-00-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Fan, Wei; Wu, Yong; Li, Xian-Kun; Yao, Nian; Li, Xun; Yu, Yong-Guo; Hai, Li; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3651 – 3661;,
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3622-23-9, 2,6-Dichloro-1,3-benzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,3622-23-9

A mixture of 2,6-dichlorobenzothiazole (1.0 g, 4.9 mmol) and 2-fluoro-4-iodoaniline (2.32 g, 9.8 mmol) in 20 mL BuOH was stirred at 90 C., and then HCl (4 M in dioxane, 1.0 mL) was added. The reaction mixture was stirred with heating at 90 C. overnight, under argon. NMR analysis then showed little 2,6-dichlorobenzothiazole remaining. After BuOH was removed by rotary evaporation, EtOAc (100 mL) and 1 N aqueous HCl (100 mL) were added. The organic layer was separated and washed with 1 N aqueous HCl (100 mL), saturated Na2O2S3 solution (50 mL), water (100 mL), and then dried over Na2SO4. Removal of solvent under reduced pressure afforded a residue, which was triturated with EtOAc (10 mL) and hexanes (40 mL). The solid was filtered and dried in vacuo to a constant weight, to afford the desired product as a light purple solid (0.75 g, 38%). 1H NMR (DMSO-d6) delta 10.45 (s, 1H), 8.35 (t, 1H), 7.95 (s, 1H), 7.70 (d, 1H), 7.58 (d, 2H), 7.30 (d, 1H).

As the paragraph descriping shows that 3622-23-9 is playing an increasingly important role.

Reference£º
Patent; Bayer Pharmaceuticals Corporation; US2004/224997; (2004); A1;,
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72850-79-4, Ethyl 2-bromo-4-(trifluoromethyl)thiazole-5-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,72850-79-4

A mixture of 2-bromothiazole 8 (152 mg, 0.50 mmol), Et3N (0.28 mL, 2.0 mmol, 4.0 equiv) and the appropriate isothiouronium salt (233 mg, 1.0 mmol, 2.0 equiv) were heated using MW irradiation at 130 C for 30 mins. The solvent was removed under reduced pressure and the orange residue was reconstituted in EtOH (5 mL) and treated with LiOH¡¤H2O (107 mg, 2.55 mmol, 5.1 equiv) for 5 h. The reaction mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (10 mL) and H2O (10 mL). The isolated aqueous phase was made acidic (pH = 1) using 2 M HCl (ca. 3 mL) and extracted using CH2Cl2/EtOH (9:1, 4 ¡Á 10 mL). The combined organic extract was dried (MgSO4), filtered and concentrated to give the title compound (75 mg, 43%) as a white powder;

72850-79-4 Ethyl 2-bromo-4-(trifluoromethyl)thiazole-5-carboxylate 13282759, athiazole compound, is more and more widely used in various fields.

Reference£º
Article; Hickey, Shane M.; White, Jonathan M.; Pfeffer, Frederick M.; Ashton, Trent D.; Synlett; vol. 26; 12; (2015); p. 1759 – 1763;,
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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.169260-97-3,5-(Trifluoromethyl)thiazol-2-amine,as a common compound, the synthetic route is as follows.

General procedure: The carboxylic acid in question (0.55 mmol), the amine in question (0.50 mmol),1 -hydroxy-7-azabenzotriazole (HOAt, 0.75 mmol) and 1 -ethyl-3-(3-di methylaminopropyl)carbodiimide (EDO, 0.55 mmol) were dissolved in 6 mL of DMF. The resulting slurry was stirred for 24h at ambient temperature. Thereafter 3 mL of methanol and 0.2 g of silica gel 018 were added sequentially and the mixture was stirred for 2 h, thenfiltered and solid residue dissolved in 0.5-1 mL of DMSO for HPLC purification (H20:MeOH), gradient). Yield: 20- 80%., 169260-97-3

169260-97-3 5-(Trifluoromethyl)thiazol-2-amine 15388849, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; WILL, David William; REID, George; CHARAPITSA, Iryna; LEWIS, Joe; (118 pag.)WO2018/229195; (2018); A1;,
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55690-60-3, 5-Methoxybenzo[d]thiazole-2-thiol is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

55690-60-3, A mixture of 5-methoxy-1,3-benzothiazole-2-thiol (500 mg), thionyl chloride (2 mL) and DMF (1 drop) was stirred at 50 C. for 3 days. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (211 mg).1H NMR (300 MHz, DMSO-d6) delta 3.84 (3H, s), 7.15 (1H, dd, J=9.0, 2.5 Hz), 7.53 (1H, d, J=2.5 Hz), 7.97 (1H, d, J=9.0 Hz).

The synthetic route of 55690-60-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Yamashita, Tohru; Kamata, Makoto; Hirose, Hideki; Murakami, Masataka; Fujimoto, Takuya; Ikeda, Zenichi; Yasuma, Tsuneo; Fujimori, Ikuo; Mizojiri, Ryo; Yukawa, Tomoya; US2011/263562; (2011); A1;,
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Thiazole | chemical compound | Britannica

57268-16-3, 5-Bromo-2-methylthiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

57268-16-3, A sol. of intermediate 7 (0.070 g, 0.14 mmol), 5-bromo-2-methylthiazole (0.051 g, 0.29 mmol), Cs2CO3 (0.047 g, 0.14 mmol), Pd(PPh3)4 (0.033 g, 0. 29 mmol) and a 3 N NaOH aq. sol. (0.024 ml, 0.07 mmol) in 1,4-dioxane (10 ml) was purged with N2 for 2 min. The r.m. was stirred at 80 0C overnight. After cooling, H2O was added and the product was extracted with DCM. The organic phase was washed with brine, dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC [RP Shandon Hyperprep Cl 8 BDS (8 mum, 250 g, LD. 5 cm); mobile phase: (0.25 % NH4CO3 sol. in water, MeOH + CH3CN)]. The product fractions were collected and concentrated under reduced pressure. Yield: 0.013 g of compound 4 (19.7 %).

57268-16-3 5-Bromo-2-methylthiazole 13228663, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); A1;,
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