Heterocyclic Building Blocks-Thiazole

131106-70-2, 6-(Trifluoromethyl)benzo[d]thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0.05 mole of 6-trifluoromethylbenzothiazole was added to 20 ml of ethyl ether at a temperature ranging -65 to -55 C. On the other hand, 0.05 mole of n-butyl lithium was added to 155 ml of ethyl ether. The former mixture was added to the latter one in a dropwise fashion for 15 minutes. In addition, 0.05 mole of triphenyl bromosilane was added to 20 ml of ethyl ether. This solution was added to the above mixed solution in a dropwise fashion at -45 C. for 5 minutes. It was heated up to -13 C. for 4 hours and maintained at a temperature of -13 to -10 C. for 4 hours. Then, an aqueous ammonium chloride solution and ice were added to the resulting solution to separate an ethyl ether layer. The separated ethyl ether layer was washed with water, dried with sodium sulfate, and treated under reduced pressure to remove a solution. Then, a semi-solid phase material was extracted with 300 ml of boiling petroleum and treated under reduced pressure to remove the solution. When the solution was removed, the extract was washed with 50 ml of ethanol and 15 ml of benzene and then, recrystaled with a mixture of 6 ml of benzene and 15 ml of ethanol to thereby produce a yellow solid at a yield of 23%.

131106-70-2, The synthetic route of 131106-70-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SAMSUNG ELECTRONICS CO., LTD.,; Industry-University Cooperation Foundation, Hanyang University; US2008/207905; (2008); 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.64987-16-2,Methyl 2-(2-aminothiazol-4-yl)acetate,as a common compound, the synthetic route is as follows.,64987-16-2

sodium metal, batch into 100ml refined anhydrous methanol, and continue to stir.To be sodiumAfter all was dissolved, 34.4 g (0.2 mol) of methyl 2-amino-4-thiazoleacetate was pre-dissolved in 200 ml of purified anhydrous methanol and added dropwise to a solution of sodium methoxide; 37.6 g of 2,6-dichloropurine0.2mol) was pre-dissolved in 200ml refined anhydrous methanol, slowly added dropwise to the reaction mixture, stirred at reflux, TLC followed by reaction, the reaction was completed, the column was separated and evaporated to dryness under reduced pressure to give a light yellow solid 33.8g, Yield 52.0%.

As the paragraph descriping shows that 64987-16-2 is playing an increasingly important role.

Reference：
Patent; Nanchang University; Mai Xi; Feng Lihua; Liao Yijing; Xu Zhaoxing; (7 pag.)CN107513064; (2017); A;,
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.4175-72-8,4-Chlorothiazole,as a common compound, the synthetic route is as follows.,4175-72-8

Under nitrogen, a solution of 4-bromophenyl acetate (compound 29.2, 1.08 g, 5.02 mmol), 4-chlorothiazole (compound 29.3, 600 mg, 5.02 mmol), Pd(OAc)2 (114 mg, 0.500 mmol), K2C03 (1.06 g, 7.53mmol), PivOH (0.17mL, 1.51mmol) and PCy3.HBF4 (369 mg, 1.00 mmol) in DMA (3mL) was stirred at 100C for 2 hours. The resulting solution was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SC>4 and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (gradient: 0%-20% ethyl acetate /petroleum ether) to afford compound 29.4, 380 mg (30% yield) as a light yellow solid. LCMS (ESI): [M+H]+ = 254. XH NMR (300 MHz, DMSO-i) delta 9.18 (s, 1H), 7.78 – 7.67 (m, 2H), 7.36 – 7.25 (m, 2H), 2.32 (s, 3H).

As the paragraph descriping shows that 4175-72-8 is playing an increasingly important role.

Reference：
Patent; GENENTECH, INC.; DRAGOVICH, Peter; GAZZARD, Lewis J.; PILLOW, Thomas; SADOWSKY, Jack; STABEN, Steven T.; WAI, John Sui-Man; (399 pag.)WO2019/84030; (2019); 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.31785-05-4,Ethyl 5-amino-2-methylthiazole-4-carboxylate,as a common compound, the synthetic route is as follows.

A solution of ethyl 5-amino-2-methylthiazole-4-carboxylate (1.7 g, 9.0 mmol), 1-bromo-2- methoxyethane (1.2 g, 9.0 mmol) and Cs2CO3 (4.4 g, 13.5 mmol) in DMF (10 mL) was heated to 50C for 7 hours and then cooled to r.t. The crude product was purified by reverse phase C18 column chromatography (MeCN/H2O) to give ethyl 5-((2-methoxyethyl)amino)-2- methylthiazole-4-carboxylate as an orange oil (850 mg, 3.48 mmol, 39%). ESI-MS m/z: 245.2 [M+H]+., 31785-05-4

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

Reference：
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; LIN, Kai; RHODIN, Michael, H.J.; McALLISTER, Nicole, V.; OR, Yat, Sun; (447 pag.)WO2019/67864; (2019); 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.

In a suspension of 6-bromobenzo[dlthiazol-2-amine (500 mg, 2.2 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi( 1 ,3,2-dioxaborolane) (1.1 g, 4.4 mmol), Pd(dppf)C12 (161 mg, 0.2 mmol) and KOAc (754 mg, 7.7 mmol) in 20 mL of dioxane was stirred at 100 C under N2 overnight. The reaction was filtered. And the filtrate was evaporated to give the title compound as a black oil (1.5 g)., 15864-32-1

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

Reference：
Patent; ZHANG, Xiaohu; ACCRO BIOSCIENCE INC.; MA, Haikuo; ZHENG, Jiyue; HE, Sudan; (101 pag.)WO2018/237370; (2018); 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.615-20-3,2-Chlorobenzothiazole,as a common compound, the synthetic route is as follows.

615-20-3, To a solution of 2-CHLOROBENZOTHIAZOLE (12.0 g, 70.7 MMOL) in concentrated H2SO4 (60 mL) was added HN03 (69percent solution, 6 mL) dropwise at 0°C for 20 min. The mixture was stirred at 5°C for 3h, poured into ice-water (150 mL). The precipitate was collected and washed with 5percent sodium bicarbonate and water, dried in VACUO.APOS;H NMR analysis showed the mixture contained 78percent 6-nitro-2-chlorobenzothiazole and 8percent 5-nitro-2- chlorobenzothiazole. Recrystallization from ethanol gave 6-nitro-2-chlorobenzothiazole as white crystalline solid (11 g, 72percent). 3.5 g of the solid was dissolved in refluxing ethanol-acetic acid (150: 15 mL), Iron powder was added in one portion.. The mixture was refluxed for 1.5h, filtered. The filtrate was concentrated in vacuo to half volume and neutralized with 10percent NaOH to pH 7.5, extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to give a residue, which was RECRYSTALLIZED from ethanol. Light purple crystals (2.5 g, 83percent) were obtained. Mp 160-164°C ; TLC single spot at Rf 0.27 (30percent EtOAc/hexane) ;APOS;HNMR (270 MHz, DMSO-d6) 5 7.58 (1H, d, J = 9.0 Hz, 4-H), 7.03 (1H, d, J = 2.0 Hz, 7-H), 6.77 (1 H, dd, J = 9.0, 2. 0 Hz, 5-H), 5.55 (2H, s, NH2). The mother liquor from the RECRYSTALLIZATION of nitration product was evaporated and subjected to iron powder reduction as described above. The crude product was purified with flash chromatography (ethyl acetate-DCM gradient elution) to give 2-CHLORO- benzothiazol-5-yl-amine as yellow solid. Mp 146-149°C ; TLC single spot at Rf 0.52 (10percent EtOAc/DCM) ;APOS;HNMR (270 MHZ, DMSO-d6) 8 7.63 (1 H, d, J = 8. 6 HZ, 7-H), 7.05 (1 H, d, J = 2.3 Hz, 4-H), 6.78 (1 H, dd, J = 8.6, 2.3 Hz, 6-H), 5.40 (2H, s, NH2).

As the paragraph descriping shows that 615-20-3 is playing an increasingly important role.

Reference：
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

15864-32-1, 2-Amino-6-bromobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-Amino-5-bromo-benzenethiol. 6-Bromo-benzothiazol-2-ylamine (Ig) was dissolved in ethylene glycol (4 mL) treated with KOH aq. (4 mL, 10M) and heated to 125 deg. C for 12 hours. The reaction was cooled, filtered, neutralized with HOAc and the solvents removed. The resulting mixture was redissolved in 5 mL of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. MS: 204.5 (M+H+)., 15864-32-1

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

Reference：
Patent; GENELABS TECHNOLOGIES, INC.; WO2008/70447; (2008); A2;,
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.103878-58-6,5-Bromothiazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

(b) 5-bromo-N-cyclopropyl- 1, 3-thiazole-4-carboxam ide To a solution of 5-bromo-1,3-thiazole-4-carboxylic acid (3.09 g, 14.85 mmol) in DCM (75 mL) was added DIPEA (5.17 mL, 29.71 mmol) followed by cyclopropylamine (1.18 mL, 17.08 mmol) and HATU (6.21 g, 16.34 mmol). The reaction mixture was allowed to stir at room temperature for 6 h. The mixture was then diluted with H20 (50 mL) and the layers were separated. The aqueous layer was further extracted with DCM (3 x 25 mL) and the combined organics dried over MgSO4, filtered and concentrated under reduced pressure. The crude reaction product was purified by flash chromatography eluting with a gradient system of 0-50% EtOAc in Petroleum ether (40-60) to give 5-bromo-N-cyclopropyl-1,3- thiazole-4-carboxamide (2.88 g, 78 % yield) as a white solid. LC-MS (Method D) 247.2/249.2 [M+H] RT 1.82 mm

103878-58-6, The synthetic route of 103878-58-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; REDX PHARMA PLC; RATCLIFFE, Andrew; HUXLEY, Anthony; LYTH, David; NOONAN, Gary; KIRK, Ralph; UOSIS-MARTIN, Mario; STOKES, Neil; WO2015/155549; (2015); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

288-47-1, Thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 2A; 2-Bromoacetylthiazole; The following is a large-scale adaptation of the Dondoni procedure cited above. A solution of bromoacetyl bromide (57.6 g, 0.286 mol) in dry DCM (100 mL) was added at 0-60C to a stirred solution of 2-trimethylsilylthiazole (37.4 g, 0.238 mol) in DCM (300 mL). After 2h at 0 0C, aqueous saturated NaHCO3 (1 L) was added and the resulting mixture was extracted with DCM (2 x 500 mL). The extracts were stirred with decolorizing carbon (Darco KB, 10 g) and filtered through Celite, and concentrated. The residue was purified by SGC (1.2 kg silica, 1:3 to 1:1 DCM-hexanes) giving 25.2 g of colorless crystalline solid (41%). 1H NMR (CDCI3, 400 mHz) delta 8.02 (d, 1H, J = 3.3 Hz), 7.74 (d, 1H, J = 3 Hz)1 4.69 (s, 2H). An alternate preparation was also achieved as follows. A solution of n-butyllithium (13.1 mL of 2.5 M in hexanes) was added at – 78 0C to a stirred solution of 2-thiazole (2.66 g, 31.25 mmol) in ether (26 mL). After 15 mi?, methyl bromoacetate (3.11 mL, 32.8 mmol) was added giving a light brown slurry which was warmed to RT and treated with acetic acid (3.6 mL) . Water (50 mL) and ether (30 mL) were added and the ether layer was separated, dried, and concentrated. The residue was suspended in hexanes (50 mL) at reflux and the hexanes decanted from a heavy oil. This was repeated and the hexanes combined and concentrated giving 4.9 g of light yellow needles (76%) having NMR identical to that described above plus minor impurities which could be removed by one trituration with 10 mL hexanes at RT.

288-47-1, As the paragraph descriping shows that 288-47-1 is playing an increasingly important role.

Reference：
Patent; PFIZER PRODUCTS INC.; WO2008/4117; (2008); 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.1094070-77-5,tert-Butyl (2-bromothiazol-5-yl)carbamate,as a common compound, the synthetic route is as follows.

[00299] 1 , 1 -Dimethylethyl (2-bromo- 1 ,3-thiazol-5 -y l)((2S)-2-(((( 1,1- dimethylethyl)oxy)carbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propyl)-carbamate: To a 250 mL round-bottomed flask was added tert-butyl 2-bromothiazol-5-ylcarbamate (0.75 g, 2.69 mmol), DMF (26.9 mL, 2.69 mmol), and cesium carbonate (1.75 g, 5.37 mmol). The mixture was warmed to 500C and 1,1-dimethylethyl 4-((4-(trifluoromethyl)phenyl)methyl)-l,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (1.13 g, 2.96 mmol, Scheme 1) was added slowly in 10 mL DMF. After 1 hour, the mixture was cooled, diluted with ether (100 mL) and washed with brine (3×50 mL). The organic layer was dried over sodium sulfate, evaporated onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 20 % to 100 % EtOAc in hexane, to provide the product (1.42 g, 91 % yield) as a white amorphous solid. LCMS (API-ES) m/z (%): 582 (100%, M+H).

1094070-77-5, The synthetic route of 1094070-77-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AMGEN INC.; WO2009/11880; (2009); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica