Category: thiazole

31785-05-4, Ethyl 5-amino-2-methylthiazole-4-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of compound 2 (5-amino-2-methylthiazolor5,4-o1pyrimidin-7-ol): 5-amino-2-methyl-thiazole-4-carboxylic acid ethyl ester (compound 1) (31.3 g. 0.168 mol) and cyanamide (17.5 g, 0.416 mol) were dissolved in dioxane (150 ml_, pre-dried using 4 A molecular sieves). In addition, drop wise 4 N HCI in dioxane (200 ml) was added over 15 minutes and the mixture was heated to reflux and vigorously stirred, for 5 days. The volatiles were evaporated to dryness and the crude product (55 g) was used without any further purification in the next step.

31785-05-4, The synthetic route of 31785-05-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER PRODUCTS INC.; WO2008/59368; (2008); A2;,
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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.

Intermediate 1 : Formation of Lambda/-(6-bromo-1 ,3-benzothiazol-2-yl)acetamideAcetic anhydride (4.95 mL, 52.4 mmol) was added to a solution of 2-amino-6- bromobenzothiazole (3.00 g, 13.2 mmol) in anhydrous pyridine (30 ml) at 00C. The resulting mixture was stirred at RT for 48 hours. The reaction mixture was poured into water (300 mL) and stirred for 30 minutes. Then the precipitate was washed with water (5x) and dried under reduced pressure to give the title compound as a white powder (3.44 g, 97%). HPLC, Rt: 3.3 min (purity: 99.1 %). UPLC/MS, M+(ESI): 270.1 and 272.1 , M-(ESI): 269.1 and 271.1., 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
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31785-05-4,Ethyl 5-amino-2-methylthiazole-4-carboxylate,as a common compound, the synthetic route is as follows.,31785-05-4

Add a solution of ethyl 5-amino-2-methylthiazole-4-carboxylate (120g; 645 mmol) and 2-fluoronitrobenzene (68 mL; 645 mmol) in dimethylsulphoxide [(1L)] to a 2L 3-necked RB flask equipped with reflux condenser, thermometer, mechanical stirrer. Add lithium hydroxide monohydrate (54 g; 1290 mmol) to the solution and heat at [50C] for 3 hours under nitrogen. Cool the purple solution and pour onto ice/water, allow to stir for one hour, filter and wash with water, dry at [50C] under reduced pressure to give 190 g (96%) as an orange solid: mass spectrum (m/e): 308 (M+1) [; 1HNMR (300MHZ, DMSO-D6,] ppm): [8] 1.25 (tr, 3H), 2.56 (s, 3H), 4.25 (q, 2H), 7.20 (m, [1H),] 7.78 (m, 2H), 8.20 (d, 1H), 11.42 (s, 1H, NH). [13CNMR] (75MHz, DMSO, ppm): [5] 24.4, 29.2, 71.2, 127.8, 132.5, 132.8, 137.8, 146.5, 147.0, 147.5, 160.2, 161.5, 173.7. Formula : C13H13N3O4S.

As the paragraph descriping shows that 31785-05-4 is playing an increasingly important role.

Reference：
Patent; ELI LILLY AND COMPANY; WO2004/14895; (2004); A1;,
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3622-35-3, Benzo[d]thiazole-6-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Production Example 9To a mixture of 5.0 g of benzothiazole-6-carboxylic acid and 50 ml of DMF was added 7.4 g of 2-fluoro-3-hydroxybenzylamine hydrobromide, 12.0 g of BOP reagent and 11.0 g of triethylamine, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate . The organic layer was washed with saturated saline, then, dried over magnesium sulfate and concentrated under reduced pressure . The resultant residue was subjected to silica gel chromatography, and 9.0 g of N- (2-fluoro-3-hydroxyphenyl) methyl-benzothiazole-6-carboxam ide was obtained.N- (2-fluoro-3-hydroxyphenyl) methyl-benzothiazole-6-c arboxamide 1H-NMR (DMSO-d6) delta: 9.78 (IH, s) , 9.54 (IH, s) , 9.13 (IH, t, J = 5.7 Hz) , 8.70 (IH, d, J = 1.7 Hz) , 8.16 (IH, d, J = 8.5 Hz) , 8.05 (IH, dd, J=8.5, 1.7Hz), 6.93 (IH, t, J=7.8Hz), 6.87-6.77 (2H, m) , 4.53 (2H, d, J = 5.6 Hz).

3622-35-3, As the paragraph descriping shows that 3622-35-3 is playing an increasingly important role.

Reference：
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/157528; (2009); A1;,
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1194374-25-8, 2-Bromo-5-methylthiazole-4-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 2-(2-Methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid; 2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6a (1.7 g, 6.08 mmol), 2-bromo-5-methyl-thiazole-4-carboxylic acid (900 mg, 4.05 mmol), tetrakis (triphenylphosphine)palladium (233 mg, 0.2 mmol) and sodium carbonate (1.29 g, 12.16 mmol) were dissolved in 30 mL of 1,4-dioxane. The reaction mixture was heated to reflux for 4 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with 20 mL of hydrochloric acid (1 N) and 30 mL of ethyl acetate. The separated organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was recrystallized from a solvent mixture of ethyl acetate and hexane to obtain the title compound 2-(2-methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid 47a (310 mg, yield 26%) as a yellow solid. MS m/z (ESI): 292.6 [M-1] 1H NMR (400 MHz, DMSO-d6): delta 13.45 (br, 1H), 8.58 (dd, J = 8.0, 1H), 8.14 (dd, J = 8.0,1H), 7.52 (t, J = 8.0, 1H), 3.93 (s, 3H), 2.71 (s, 3H), 1194374-25-8

Big data shows that 1194374-25-8 is playing an increasingly important role.

Reference：
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2236500; (2010); A1;,
Thiazole | C3H3NS – PubChem
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.118452-02-1,2-Aminothiazole-4-carboxamide,as a common compound, the synthetic route is as follows.

4. g (28 mmol) 2-Aminothiazol-4-carboxamide was dissolved in 40 ml glacial acetic acid, to which added 2.8 ml (29.6 mmol) acetic anhydride, followed by reacting under reflux for 2 hr, and naturally cooling down to precipitate a large quantity of solids, which were filtered, washed and dried to obtain 4.7 g 2-acetylaminothiazol-4-carboxamide (yield 92%) with mp>250 C., 118452-02-1

118452-02-1 2-Aminothiazole-4-carboxamide 257149, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Li, Song; Zhao, Guoming; Xia, Guangqiang; Wang, Lili; Zheng, Zhibing; Xie, Yunde; Zhong, Wu; Xiao, Junhai; Li, Xingzhou; Cui, Hao; US2010/87448; (2010); A1;,
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14527-43-6, Ethyl thiazole-4-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 13 (108.25?g, 0.689?mol) in THF (344?mL) was added dropwise to a suspension of LiAlH4 (26.3?g, 0.692?mmol) in THF (344?mL) at 0?C. The reaction mixture was stirred for 30?min?at 0?C (at this point TLC indicated consumption of the SM). It was then quenched by successive addition of EtOAc (50?mL), water (26?mL), 10% NaOH (26?mL) solution, and water (78?mL) (the temperature should not exceed 0?C). The precipitate was filtered and washed several times with THF. The filtrate was evaporated to give 8, which was used without purification. M?=?43.25?g. Yield?=?54%., 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

3622-35-3, Benzo[d]thiazole-6-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

After adding benzothiazole-6-carboxylic acid (5.0 g, 27.9 mmol), HATU (15.9 g, 41.9 mmol) and DIPEA (11.7 mL, 83.7 mmol) to dichloromethane (87 mL) and N,N-dimethylformamide (22 mL), the result was stirred for 30 minutes. To the reaction solution, an N,O-dimethylhydroxylamine salt (3.0 g, 30.7 mmol) was introduced, and the result was stirred for 12 hours at room temperature. After terminating the reaction, the reaction solution was removed, and ethyl acetate was added thereto. The result was washed with water and saline, then dried using anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and purified using column chromatography to obtain a target compound (6.2 g). 1H NMR spectrum (300 MHz, CDCl3) delta 9.13(s, 1H), 8.36(d, 1H), 8.16(d, 1H), 7.87(dd, 1H), 3.57(s, 3H), 3.42(s, 3H).

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; Hanmi Pharmaceutical Co., Ltd.; LEE, Kyung Ik; JUNG, Young Hee; SONG, Ji Young; JUN, Seung Ah; (89 pag.)EP3480193; (2019); A1;,
Thiazole | C3H3NS – PubChem
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19989-67-4,Benzo[d]thiazole-6-carbaldehyde,as a common compound, the synthetic route is as follows.

To a mixture of compound B-184 (2.5 g, 15 mmol) in 50% ethanol/water (20 mL) was added hydroxylamine hydrochloride (2.1 g, 30 mmol) and potassium carbonate (4.2 g, 30 mmol) at room temperature. The mixture was stirred at room temperature overnight. On completion, the reaction was filtered, and the resulting filtrate was concentrated in vacuo and purified by silica gel column chromatography [petroleum ether : ethyl acetate = 20: 1] to give compound B-185 (2.3 g, 84% yield) as a white solid., 19989-67-4

The synthetic route of 19989-67-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (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.15864-32-1,2-Amino-6-bromobenzothiazole,as a common compound, the synthetic route is as follows.

Preparation Example 17; Preparation of Compound (17); Under argon atmosphere, 2-amino-6-bromobenzothiazole (20 g, 87.3 mmol) and 10 N KOH (100 mL) were added to ethylene glycol (20 mL), and the mixture was stirred at 125 C. under reflux for 15 hours. After cooling to room temperature, 12 N HCl (30 mL) was added to the reaction mixture to quench the reaction. The reaction mixture was then washed with water (100 mL) and extracted with EA (100 mL). Recrystallization from MeOH (200 mL) gave 2-amino-5-bromobenzenethiol (14 g, 68.6 mmol, 79%).In 1,4-dioxane (35 mL, 2.0 M), dissolved were 2-amino-5-bromobenzenethiol (14 g, 68.6 mmol) and salicylaldehyde (7.0 g, 57.2 mmol), and the solution was stirred at 100 C. under pressure for 12 hours. After cooling to room temperature, the reaction mixture was extracted with MC (150 mL), washed with water (100 mL) and dried under reduced pressure. Purification via silica gel column chromatography (n-hexane: MC=5:2) gave 2-(6-bromobenzo[d]thiazol-2-yl) phenol (15.5 g, 50.5 mmol, 88.3%).Under argon atmosphere, 2-(6-bromobenzo[d]thiazol-2-yl)phenol (15.5 g, 50.5 mmol) was dissolved in THF (160 mL, 0.3 M), and the solution was cooled to -78 C. To the solution, t-BuLi (1.7 M in hexane, 44.6 mL, 75.8 mmol) was added dropwise, and the mixture was stirred for 30 minutes. Triphenylsilyl chloride (TPSCl) (22.3 g, 75.8 mmol) dissolved in THF (50 mL) was slowly added thereto. The reaction mixture was stirred for 12 hours while slowly raising the temperature to room temperature. After quenching the reaction by adding water (100 mL), the reaction mixture was extracted with MC (80 mL). Drying under reduced pressure and purification via silica gel column chromatography (n-hexane: MC=3:1) gave 2-(6-triphenylsilylbenzo[d]thiazol-2-yl)phenol (20.4 g, 42 mmol, 83%).Compound (17) (1.0 g, 0.72 mmol, 45%) was obtained by repeating the same procedure as described in Preparation Example 1, but using 2-(6-triphenylsilylbenzo[d]thiazol-2-yl)phenol (2.0 g, 4.1 mmol), ZnCl2 (375 mg, 2.7 mmol), EtOH (70 mL, 0.02 M), NH4OH (2.0 mL) and water (20 mL).mp. >300 C.1H NMR (300 MHz, CDCl3): d=8.40-8.34 (m, 2H), 7.83-7.55 (m, 7H), 7.35 (s, 9H), 7.31 (d, J=5.1 Hz, 1H), 7.0-6.7 (m, 3H)MS/FAB: 1580.22 (found), 1584.77 (calculated), 15864-32-1

The synthetic route of 15864-32-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Gracel Display Inc.; US2010/152455; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica