Category: thiazole

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
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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.

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
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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;,
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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;,
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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;,
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494769-34-5, N-Boc-2-Amino-4-formylthiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Synthesis of N-tert-butyl-alpha-[2-N-(1,1-dimethylethoxycarbonyl) aminothiazol-4-yl]nitrone (28) 2.0 g (8.76 mmol) of compound 22, 5.42g (52.57 mmol) of 2-methyl-2-nitropropane (27), and 2.86 g (43.81 mmol) of zinc were placed in a round-bottomed flask along with 95% ethanol (50 mL) and cooled to 0 C. 4.21 g (70.11 mmol) of acetic acid was added slowly with stirring. The solution was allowed to come to room temperature, stirred for 6 hours. CH2Cl2 was added to the reaction mixture and it was filtered through a Celite pad and concentrated under reduced pressure. The residue was purified by short flash column chromatography (silica, Hex_EtOAc=1:1) to give 1.28 g (4.28 mmol) of compound 28 as a yellow solid in 49% yield. 1H NMR (CDCl3): 9.9 (br s, 1H), 8.82 (s, 1H), 7.87 (s, 1H), 1.60 (s, 9H), 1.54 (s, 6H); 13C NMR (CDCl3): 159.54, 152.35, 141.53, 125.78,

494769-34-5, 494769-34-5 N-Boc-2-Amino-4-formylthiazole 23138686, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Ko, Sung-Bo; Oh, Eu-Gene; Kim, Eon-Kyeom; Kim, Won-Yeob; Choi, Dennis W.; Dugan, Laura L.; Koh, Jae-Young; Won, Moo-Ho; Wie, Myung-Bok; US2003/220337; (2003); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14542-13-3,2-Methoxythiazole,as a common compound, the synthetic route is as follows.

14542-13-3, Production Example 36 Synthesis of (2-methoxy-5-thiazolyl)ethyl bromide 2-Methoxythiazole (3.9 g) was treated as in the above Production Example 35 to give the title compound (1.4 g) as a brown oil (yield: 19%). 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.20(2H, t, J=7Hz), 3.51(2H, t, J=7Hz), 4.03(3H, s), 6.89(1H, s).

The synthetic route of 14542-13-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
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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-N?-(2-(5,7-difluoro-1-tosyl-1H-indol-3-yl)-6-phenylpyrimidin-4-yl)cyclohexane- 1,3 -diamine (50 mg, 0.09 mmol) and2-aminothiazole-4-carboxylic acid (27 mg, 0.19 mmol) in a mixed solvent of dimethyl sulfoxide (2 mL) and tetrahydrofuran (4 mL) was added DIPEA (46 1iL, 0.28 mmol).The mixture was stirred at rt for 10 mm then HATU (68 mg, 0.18 mmol) was added. The resulting mixture was stirred at rt overnight. To the reaction mixture was added water (30 mL), and the mixture was exttracted with ethyl acetate (30 mL x 3). The combined organic layers were washed with a saturated aqueous sodium chloride solution(60 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to give the title compound as a light yellow solid (89 mg), which was used in the next step without further purification.

40283-41-8, As the paragraph descriping shows that 40283-41-8 is playing an increasingly important role.

Reference：
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; ZHANG, Yingjun; (264 pag.)WO2018/33082; (2018); 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.64987-16-2,Methyl 2-(2-aminothiazol-4-yl)acetate,as a common compound, the synthetic route is as follows.

64987-16-2, Each of Compounds 36 and 37 was synthesized as follows. Reaction of an amino substituted heteroaryl with (trimethylsilyl) diazomethane (2.0 M solution in hexanes) in a solvent of methanol and benzene yielded an intermediate. Substitution of the intermediate at C-4 position of DBD gave the desired product. See Scheme 2 below. Analytical data on Compound 36 are shown below. Compound 36, i. e., [4′-O-DEMETHYL-4 – [4″- (METHYL-O-ACETYL)-2″-] thiazolylamino] -4-desoxypodophyllotoxin. Yield 59%; Amorphous, mp [116-120 C] (dec. ); ESI MS: 553 [M-H], 577 [[M+NA]. LH] NMR [(CDC13)] [6] 6.85 (s, 1H, 5-H), 6.52 (s, 1H, 8-H), 6.38 (s, 1H, 5″-H), 6.30 (s, 2H, 2′, 6′-H), 5.98 and 5.96 (dd, 2H,- [OCH70-),] 5.16 (br, 1H, 4-H), 4. 59 (br, [1H,] 1-H), 4.40 (t, [1H, 11-H),] 3.95 (t, [1H,] 11- H), 3.79 (s, 6H, 3′, 5′-OCH3), 3.73 (s, 3H,-COOCH3), 3.60 (s, [2H,-CHACOOCH3),] 3.00 (m, 2H, 2-H, 2-H). Compounds 6,11, 38-42,77-82, 84,96, 118,126, 128,130-131, 140,145- 146,163, and 165 were synthesized by coupling an appropriate alcohol or amine to an amino substituted heteroaryl followed by conjugation with DBD. Analytical data on a number of compounds are shown below. Compound 39, i. e., [4′-O-DEMETHYL-40- [5″- (ETHOXYCARBONYL)-2″-] pyridylamino)]-4-desoxypodophyllotoxin. Yield 35 %; Amorphous, mp [164-168 C] (dec. ); ESI MS: 547 [M-H], 571 [[M+NA]. LH] NMR [(CDC13)] [S] 8.78 (d, 1H, [J] = 2.2 Hz, 6″-H), 8.04 and 8.01 (dd, J = 2.2 Hz, 1H, 4″-H), 6.79 (s, 1H, 5-H), 6.55 (s, 1H, 8- H), 6.42 (d, [J =] 8.8 Hz, [1H,] 5″-H), 6.33 (s, 2H, 2′, 6′-H), 5.99, 5.96 (dd, J = 1. 6 Hz, [2H,-OCHEO-),] 5.46 (br, 2H, 4-H, [NH),] 4.88 (d, J = 5.5 Hz, 1H, 1-H), 4.62 (br, 1H, [11-H),] 4.40 (br, [1H, 11-H),] 4. [36] (q, J = 7.1 Hz, 2H, [CH2CH3),] 3.79 (s, 6H, 3′, 5′- OCH3), 3.03 (m, 2H, 2-H, 2-H), 1.36 (t, J = 7.1 Hz, 3H, CH2CH3). Compound 84, i. e., [4′-O-DEMETHYL-40- [4″- (ETHOXYCARBONYL)-3″-] pyrazolylamino] -4-desoxypodophyllotoxin. Yield 40 %; White solid, mp [152-155 C] [(DEC.) ; ESI] MS: 536 [M-H]. 1H NMR [(CDC13)] [8] 7.32 (s, 1H, 5″-H), 6.66 (s, 1H, 5- H), 6.62 (s, [1H,] 8-H), 6.31 (s, 2H, 2′, 6′-H), 6.01, 6.00 (dd, J = 1. 1 Hz, [2H,-OCH70-),] 5.45 (s, 1H, NH), 5.43 (d, J = 4.9 Hz, [1H,] 4-H), 4.70 (d, J = 4.9 Hz, [1H,] 1-H), 4.68 (br, 1H, [11-H),] 4.36 (br, [1H,] [11-H),] 4.25 (m, 2H, [CH2CH3),] 3.79 (s, 6H, 3′, 5′- [OCH9,] 3.55 (m, 1H, 3-H, ), 3.25 (dd, J = 4.9 Hz, 1H, 2-H, ), 1.35 (t, J = 7.1 Hz, 3H, CH2CH3). Compound 140, i. e., [4′-O-DEMETHYL-4ss-[2″-(3″-(2″‘-CHLORO-4″‘-] pyridinylamino-carbonyl))-pyridinlylamino]-4-desoxypodophyllotoxin. Amorphous, mp > 240 C (dec); ESI MS: 630.0 [(M-1)] [;’H] NMR 6 (400 MHz, [CDC13)] : 8.65 [(1H,] d, J = 2.3 Hz, 3″‘-H of second pyridine), 8.32 [(1H,] d, J = 5.5 Hz, [6″‘-H] of second pyridine), 7.95 [(1H,] dd, J = 2.3, 9.0 Hz, 4″-H of first pyridine), 7.76 [(1H,] d, J = 2.0 Hz, 6″-H of first pyridine), 7.48 [(1H,] dd, J = 2.0, 5.9 Hz, 5″‘-H of second pyridine), 6.79 [(1H,] s, 5-H), 6.56 [(1H,] s, 8-H), 6.50 [(1H,] d, J = 9.0 Hz, 3″-H of first pyridine), 6.34 (2H, s, 2′-H, 6′-H), 5.98 (2H, d d, J = 1. 2,6. 7 Hz,-OCH20-), 5.44 [(1H,] d. [J =] 5.5 Hz, 4-H), 4.63 (1H, d, J = 3.9 Hz, [1-H),] 4.42 (1H, dd, J = 7.0, 9.4 Hz, 113035-H), 3.80 [(1H,] d, J = 2.2, 8.8 Hz, 2-H), 3.80 (6H, s, 3′, 5’-OCH3), 3.50 [(1H,] m, 3-H), 3.03 (1H, br. d, J = 4.7 Hz, 11ss-H).

64987-16-2 Methyl 2-(2-aminothiazol-4-yl)acetate 738059, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; PLANTACEUTICA INC.; WO2004/33423; (2004); 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.2941-58-4,2-Bromo-6-methoxybenzothiazole,as a common compound, the synthetic route is as follows.

A mixture of 2-bromo-6-methoxy-benzothiazole (1.14 g), 5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridin-2-amine (1.23g, 1.2 eq.)5 Pd(dppf)Cl2*DCM (170 mg, 0.05 eq.) and 2.0 M aq. K2CO3 (10 ml, 4 eq.) in DMF(20 ml) was heated at 80 0C for 2 h under o argon while stirring. Ethyl acetate (200 ml) was subsequently added before concentrating the sol. onto diatomaceous earth in vacuo. Purification by flash chromatography (DCM:methanol, 99:1 to 95:5) provided the title compound (730 mg) as a yellow solid. 1H NMR delta 8.56 (d, 1 H) 7.96 (dd, 1 H) 7.82 (d, 1 H) 7.64 (d, 1 H) 7.07 (dd, 1 H) 6.67 (br. s, 2 H) 6.55 (d, 1 H) 3.83 (s, 3 H); MS m/z (M+H) 258.1., 2941-58-4

2941-58-4 2-Bromo-6-methoxybenzothiazole 11218765, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; ASTRAZENECA AB; WO2007/86800; (2007); A1;,
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Thiazole | chemical compound | Britannica