Heterocyclic Building Blocks-Thiazole

1477-42-5, 4-Methylbenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-methyl-2-aminobenzothiazole (164 mg, 1.0 mmol) in dichloromethane (20 mL) was added 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide (EDC) (191 mg, 1.0 mmol) and 1-hydroxy-1,2,3-benzotriazole (HOBt) (13.5 mg, 0.1 mmol). Then added 2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetic acid (2) (402 mg, 0.1 mmol) and the reaction mixture was stirred at a temperature of 25 C. for 24 h and the reaction was monitored by TLC. Then to this water is added and extracted with dichloromethane. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate and hexane as solvent system to obtain the pure product (9k) (440 mg, 80% yield) 1H NMR (CDCl3): delta 10.71 (br s, 1H), 7.76 (d, 1H, J=15.4 Hz), 7.65-7.70 (m, 1H), 7.32-7.43 (m, 4H), 7.28 (s, 2H), 7.22-7.26 (m, 1H), 7.02 (d, 1H, J=8.4 Hz), 4.86 (s, 2H), 4.09 (s, 3H), 3.96 (s, 6H), 3.94 (s, 3H), 2.67 (s, 3H); ESIMS: 549 (M+1)+.

1477-42-5, The synthetic route of 1477-42-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ahmed, Kamal; Reddy, Adla Malla; Paidakula, Suresh; Rao, Neigapula Sankara; Shetti, Rajesh V. C. R. N. C.; US2013/317231; (2013); 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.687636-93-7,2-Bromothiazole-5-methanol,as a common compound, the synthetic route is as follows.

687636-93-7, EXAMPLE 4; Commercially available 2-bromo-5-formylthiazole (5 g, 26 mmol) in tetrahydrofuran (50 mL) was cooled to 0 0C. To this solution was added portionwise, sodium borohydride (1.23 g, 32 mmol), and the reaction mixture was stirred for 1 h at 0 0C, and then allowed to warm to room temperature and stirred for another hour. Upon reaction completion, water (100 ml) was added and the mixture was allowed to stir for 30 minutes. The reaction mixture was concentrated in vacuo and purified via flash chromatography (Biotage 40M). To the corresponding thiazole-alcohol (3.87 g, 20 mmol) in CH2Cl2 (10OmL) at 0 0C was added carbon tetrabromide (13.2 g, 40 mmol) and triphenylphosphine (10 g, 40 mmol). The reaction mixture was allowed to stir at room temperature for 1 h. The mixture was concentrated in vacuo and purified via flash chromatography (Biotage 40 M). To a pre-cooled (0 0C) solution containing commercially available ethyl N-(diphenylmethylene) glycinate (2.87 g, 10.7 mmol) in tetrahydrofuran (18 mL), was added potassium tert-butoxide (1.2 g, 10.7 mmol) in tetrahydrofuran (25 mL). The reaction mixture was stirred at this temperature for 30 minutes and cooled to -78 0C. To this pre-cooled (-780C ) solution was added the thiazolyl bromide (1.83g, 7.1 mmol) in tetrahydrofuran (8 mL). The reaction mixture was stirred at this temperature for 30 minutes, and then allowed to stir at room temperature for 1 h. A saturated solution of ammonium chloride (40 mL) was then added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 x 50 mL). The organic layers were combined, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography (Biotage 40M). To the corresponding Schiff base (3.17 g, 7.1 mmol) was added concentrated hydrochloric acid (9 mL), and the reaction mixture was allowed to stir for 1 h at room temperature. Following the completion of the reaction, the aqueous layer was washed 3 times with ethyl acetate (2OmL), and the aqueous layer was concentrated in vacuo. Without further purification, the amine (1.99g, 7.16 mmol) in CH2Cl2 (100 mL) was treated with triethylamine ( 2.89g, 29 mmol) and di- tert-butyl dicarbonate (3.1g, 14.3 mmol). The reaction mixture was stirred for 12 h at room temperature. Upon reaction completion, a saturated solution of sodium bicarbonate (100 mL) was added, and the mixture was allowed to stir for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (2 x 50 mL). The organic layers were combined, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography (Biotage 40 M). To the amino acid (0.82g, 2.1 mmol) in toluene (20 mL) was added (2- chloro-4-methoxyphenyl)boronic acid ( 0.81 g, 4.3 mmol), tetrakis-triphenylphosphine palladium (0.12 g, 0.1 mmol), and potassium carbonate (0.89 g, 6.4 mmol). The reaction mixture was heated to 100 0C for 12 h. Following the reaction completion, the mixture was concentrated in vacuo and purified via flash chromatography (Biotage 40M). To the desired amino acid (0.57g, 1.3 mmol) in tetrahydrofuran (6 mL) was added water (6 mL), methanol (1 mL), and lithium hydroxide (0.12 g, 5.2 mmol). The biphasic reaction mixture was allowed to stir at room temperature for 12 h. The mixture was concentrated in vacuo, diluted with 10 mL of water, cooled to 0 0C and acidified with concentrated HCl to a pH of 3. The acidic solution was extracted three times with ethyl acetate (10 mL), and the organic extracts were dried with sodium sulfate and concentrated in vacuo. Without further purification, the carboxylic acid (0.14 g, 0.33 mmol) in tetrahydrofuran (5 mL) at -20 0C was treated with 4-methylmorpholine (0.067 g, 0.67 mmol), followed by the dropwise addition of isobutyl chloroformate (0.045 g, 0.33 mol). The reaction mixture was stirred for 10 minutes, followed by the addition of ethyl-2-aminobenzoate (0.11 g, 0.67 mmol). The mixture was stirred at -20 0C for 2 h and then room temperature for 12 h. Following the reaction completion, the precipitate was filtered off and the filtrate was concentrated in vacuo and purified via flash chromatography (Biotage 40S). To the purified anthranilic acid derivative (18 mg, 33 mmol) in CH2Cl2 (3 xnL) at 0 0C, was added borontribromide (IM, 0.33 mmol). The mixture was allowed to stir at 0 0C for 10 minutes and then room temperature for 1 h. Following the reaction completion, water (10 mL) was added, and the Triphasic mixture was stirred for 10 minutes. The reaction mixture was then concentrated in vacuo, diluted with 10 mL of water, cooled to 0 0C and basified with sodium hydroxide to a pH of 14. The basic reaction mixture was allowed to stir for 12 h at room temperature. The mixture was concentrated in vacuo and then diluted with water (2 mL). The aqueous solution was acidified with concentrated hydrochloric acid (pH= 3) and then purified by reverse phase HPLC (Gilson) to provide the de…

The synthetic route of 687636-93-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2007/75749; (2007); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

768-11-6, 5-Bromobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,768-11-6

j00301j A mixture of 5-bromobenzo[djthiazole (0.34 g, 1.6 mmol), 2,4,6-trimethyl-1,3,5,2,4,6- tnoxatnbonnane (0.60 g, 4.8 mmol), dicyclohexyl-[3 -(2,4,6-triisopropylphenyl)phenyljphosphane [2- (2-aminophenyl)phenylj-chloro-palladium; (0.06 g, 0.08 mmol) and potassium phosphate (0.67 g, 3.2 mmol) in tetrahydrofuran (12 mL) and water (3 mL) at 15 C was degassed and purged with nitrogen 3 times. The mixture was stirred at 60 C for 12 hours under nitrogen, then diluted with ethyl acetate (250 mL) and washed with brine (6 x 20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give compound B-14 (0.27 g, 78% yield) as brown gum, which used directly without further purification. LCMS (Y): tR=0.633 mi, (ES) mlz (M+H) = 150.0.

As the paragraph descriping shows that 768-11-6 is playing an increasingly important role.

Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); 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.117724-63-7,2-Methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Under nitrogen atmosphere, carboxylic acid II (3mmol), EDCI (3.3 mmol), HOBT (3.3 mmol)and Et3N (1.8 mmol) were placed in a three-necked flask with 40 mL CH2Cl2, and stirred for 2 hat 0 C; then, compound I (2.4 mmol) was added to the flask and allowed to react for 3 h at 0 C.The reaction was monitored by thin-layer chromatography (TLC) (all reactions could be completed in3 h) and, on completion of the reaction, the mixture was washed with saturated NaHCO3 solutionand water, respectively. Then, it was dried over anhydrous Na2SO4, filtered and evaporated onrotavapor in vacuum. Subsequently, crude products III-1-III-18 were purified by silica gel columnchromatography [V (CH2Cl2): V (EA) = 3:1] and crude products III-19-III-36 were purified by silicagel column chromatography [V (PE): V (EA) = 3:1]. Finally, products were recrystallized with thedichloromethane/petroleum ether to obtain pure target compounds., 117724-63-7

The synthetic route of 117724-63-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhang, Shen; Meng, Siqi; Xie, Yong; Yang, Yonggui; Zhang, Yumeng; He, Lu; Wang, Kai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Li, Xinghai; Molecules; vol. 24; 14; (2019);,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

139670-03-4, 2-Bromo-4-chlorothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,139670-03-4

Isopropylmagnesium chloride lithium chloride complex solution (1.3M, 2.93 mL, 3.81 mmol) was added dropwise to a solution of 3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-N-methoxy-N-methylpropanamide (470 mg, 1.269 mmol) and 2-bromo-4-chlorothiazole (Intermediate Q) (252 mg, 1.269 mmol) in THF (20 mL). The mixture was stirred at room temperature for 45 mins. The reaction was quenched with saturated NH4Cl(aq) and extracted with EtOAc (2¡Á). The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-70% EtOAc/hexane afforded the title compound. [1052] LC-MS Rt 1.29 mins; [M+H]+ 429.2 (Method 2minLowpHv03)

139670-03-4 2-Bromo-4-chlorothiazole 15141964, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; AHMED, Mahbub; ASHALL-KELLY, Alexander; GUERITZ, Louisa; MCKENNA, Jeffrey; MCKENNA, Joseph; MUTTON, Simon; PARMAR, Rakesh; SHEPHERD, Jon; WRIGHT, Paul; US2014/171417; (2014); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica