Heterocyclic Building Blocks-Thiazole

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.

To a solution of 2-chloro-6-(trifluoromethyl)benzo[d]oxazole (500 mg, 2.26mmol) in DMF (8.0 mL) were added 2-aminothiazole-4-carboxamide (323mg, 2.26mmol) and K2003 (937mg, 6.78mmol) . The resulting mixture was stirred at 100 00 for 3 h. TLC showed the reaction to be complete. The reaction mixture was poured in to ice water (5OmL). The solid precipitated was filtered and washed with water (5OmL) and dried by azeotropic distillation using toluene. Thus obtained solid was triturated with DCM (lOmL) followed by Et20 (lOmL) and dried under vacuum. The solid was further purified by prep HPLC to afford 2-((6-(trifluoromethyl)benzo[d]oxazol-2- yl)amino)thiazole-4-carboxamide as an off white solid. Yield: 30mg (4.0%); MS (ESl+) for CHNOS m/z 328.99 [M+H] LC purity 98.0 % (Ret. Time- 5.55 mm); 1H NMR (400 MHz, DMSO-d6): 13.02 (5, 1H), 7.96 (5, 1H), 7.88 (bs, 1H), 7.78 (5, 1H), 7.58-7.73 (m, 3H).

118452-02-1, The synthetic route of 118452-02-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; DISCUVA LTD.; MEO, Dr Paul; KHAN, Dr. Nawaz; (284 pag.)WO2018/37223; (2018); A1;,
Thiazole | C3H3NS – PubChem
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96929-05-4, Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

96929-05-4, a) Boc-2-Aminomethylthiazole-4-carboxamide; [00073] At 10 C., ethyl bromopyruvate (386 g, 1.98 mol) was added dropwise to a solution of Boc-glycinethioamide (370 g, 1.94 mol) in 3.9 liters of ethanol, and the mixture was then stirred at 20-25 C. for 5 h, after which 299 ml of a 25% strength aqueous ammonia solution were added. [00074] From 940 ml of this mixture (corresponds to 19.9% of the total volume), 380 ml of ethanol were distilled off, a further 908 ml of a 25% strength aqueous ammonia solution were added and the mixture was stirred at 20-25 C. for 110 h. The mixture was cooled to 0 C. and the solid was filtered off, washed twice with water and dried. This gave 60.1 g of the BOC-protected thiazole carboxamide of an HPLC purity of 97.9 area %, which corresponded to a yield over these two steps of 60.5%. [00075] 1H-NMR (DMSO-d6, in ppm): 8.16 (s, 1H, Ar-H), 7.86 (t, broad, 1H, NH), 7.71 and 7.59 (2×s, broad, 1H each, NH2), 4.42 (d, 2H, CH2), 1.41 (s, 9H, tert-butyl).

The synthetic route of 96929-05-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Abbott GmbH & Co. KG; US6642388; (2003); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3622-35-3,Benzo[d]thiazole-6-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Carboxylic acids (1 mmol) and 1,1′-carbonyl diimidazole(1 mmol) were taken in THF (15 mL) in a round-bottommed flask(100 mL) and stirred for 30 min in order to activate the carboxylicacids. Then metronidazole (1 mmol) was added into the reactionmixture with constant stirring for 24 h. Reaction progress wasmonitored by TLC (6:4 EtOAc:Hexane). Reaction mixture waspoured onto crushed ice (100 mL), precipitates appeared immediatelywhich were filtered and dried in air. The precipitates werecrystallized from ethanol. Products were characterized by spectroscopictechniques such as EIMS, 1H NMR and 13C NMR. CHNanalysis was also performed.

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

Reference：
Article; Salar, Uzma; Khan, Khalid Mohammed; Taha, Muhammad; Ismail, Nor Hadiani; Ali, Basharat; Qurat-ul-Ain; Perveen, Shahnaz; Ghufran, Mehreen; Wadood, Abdul; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1289 – 1299;,
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Thiazole | chemical compound | Britannica

6294-52-6, 5,6-Dimethoxybenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6294-52-6

General procedure: Chloroacetyl chloride(33 mmol, 2.63 mL) was added dropwise with stirring to a mixtureof triethylamine (33 mmol, 4.63 mL) and 2-aminobenzothiazole oraniline derivative (30 mmol) in THF (100 mL) at 0 C. After thecompletion of dropping, the mixturewas allowed to stir for 1 h. Thesolvent was evaporated under reduced pressure. The residue waswashed with water to remove trimethylamine hydrochloride, driedand recrystallized from EtOH [59,60].

The synthetic route of 6294-52-6 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Sa?l?k, Beguem Nurpelin; Ilg?n, Sinem; Oezkay, Yusuf; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 1026 – 1040;,
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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.

EXAMPLE 162 (+)-(4aR)-(10bR)-4-methyl-8-(4-fluoro-2-benzothiazolylthio)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-mercapto-10b-methyl-1,2,3,4,4a,-5,6,10b-octahydrobenzo[f]quinolin-3-one (100 mg, 0.38 mmol), potassium carbonate (158 mg, 1.14 mmol), 2-chloro-4-fluorobenzothiazole (86 mg, 0.46 mmol and 1 mL of anhydrous dimethylformamide, fitted with a reflux condenser, and the stirred mixture was heated at 60, under nitrogen, for 48 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2*25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (80% ethyl acetate/hexanes eluent) to give 91 mg (58%) of the title compound as an amorphous solid. mp 140-145. FDMS: m/e=412. alpha[D]589 =+70.06 (c=0.52, chloroform)., 182344-56-5

182344-56-5 2-Chloro-4-fluorobenzo[d]thiazole 2049864, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Eli Lilly and Company; US5550134; (1996); A;,
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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.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

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;,
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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.99073-88-8,Ethyl 2-bromo-6-benzothiazolecarboxylate,as a common compound, the synthetic route is as follows.

Heat a degassed solution of ethyl 2-bromobenzothiazole-6- carboxylate (Step 1, 7.75 G, 27.1 mmol), tetrakis (TRIPHENYLPHOSPHINE) palladium (0) (1.7 g, 1.5 mmol), 4- (trifluoromethyl) phenylboronic acid (6.2 g, 32.6 mmol) and 2 M aqueous sodium carbonate solution (120 mL) in DME (90 mL) at reflux under nitrogen for 19 h. Dilute the cooled mixture with 1 N NAOH (1.2 L) and extract with methylene chloride (2 x 500 ML). Dry the combined organic extracts over MGS04, remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (98: 2), to afford ethyl 2- (4-trifluoromethylphenyl) benzothiazole-6-carboxylate as a white solid (2.62 g, 27%) : 1H NMR (CDC13) 5 1.40 (t, 3H), 4.40 (q, 2H), 7.80 (d, 2H), 8.10 (d, 1H), 8.20 (m, 3H), 8.60 (s, 1H)., 99073-88-8

The synthetic route of 99073-88-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ELI LILLY AND COMPANY; WO2004/63155; (2004); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

64987-16-2, Methyl 2-(2-aminothiazol-4-yl)acetate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,64987-16-2

A solution of methyl 2-(2-aminothiazol-4-yl)acetate (1.044 g, 5.00 mmol) and Na2CO3 (0.530 g, 5.00 mmol) in DMF (20 mL) was stirred at room temperature for 15 min. 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethan-1-one (1.852 g, 5.00 mmol) was added and mixture was stirred at 80 C overnight. Solvent was removed under reduced pressure, residue was suspended in ethyl acetate (60 mL) and successively washed with 10% citric acid (2 × 30 mL), saturated aqueous NaHCO3 solution (2 × 30 mL) and brine (30 mL), dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude product was recrystallized from methanol. Yield: 1.630 g (77.0%); white crystals; m.p. 200-202 C; 1H NMR (400 MHz, DMSO-d6): delta 3.63 (s, 3H, CH3), 3.75 (s, 2H, CH2), 7.04 (s, 1H, thiazole-H), 7.45 (d, 1H, J = 2.6 Hz, pyrrole-H), 12.42 (s, 1H, NH), 13.12 (s, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6): delta 36.4, 51.7, 98.8, 107.8, 110.8, 115.4, 125.8, 143.7, 156.6, 157.8, 170.5 ppm.

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

Reference：
Article; Campos, Ludmila E.; Garibotto, Francisco M.; Angelina, Emilio; Kos, Jiri; Toma?i?, Tihomir; Zidar, Nace; Kikelj, Danijel; Gonec; Marvanova, Pavlina; Mokry, Petr; Jampilek; Alvarez, Sergio E.; Enriz, Ricardo D.; Bioorganic Chemistry; vol. 91; (2019);,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

64987-16-2,64987-16-2, Methyl 2-(2-aminothiazol-4-yl)acetate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

thyl 2-(2-bromothiazol-4-yl)acetate Methyl 2-(2-aminothiazol-4-yl)acetate (5g, 26.8mmol) was added under nitrogen to a solution of copper(ll) bromide (6.77g, 30mmol) and f-butyl nitrite (4.79ml, 40mmol) in acetonitrile (20ml) at -20C. The reaction mixture was slowly warmed to room temperature and stirred for two hours. The solution was then diluted with diethyl ether and washed with 25ml of 10 percent hydrochloric acid solution; the aqueous phase was extracted with 20ml of diethyl ether. The combined organic phases were dried and evaporated to dryness. The residue was purified by a standard method to yield the title compound. LC-MS : m/z (M+H) = = 235.9

The synthetic route of 64987-16-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; SALITURO, Francesco G.; SAUNDERS, Jeffrey O.; TRAVINS, Jeremey; CHEN, Yongsheng; WO2014/79150; (2014); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica