Heterocyclic Building Blocks-Thiazole

56354-98-4, 6-Aminobenzo[d]thiazol-2(3H)-one is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Asolution of 2,6-difluoro-3nitropyridine (0.20g. 1.3 mrnol) and &aminobenzo[d]thiazol.-2(3H)-one (0.20 g, 1.2 mmol) in DMF (6 mL) was heated at 100 C for 1 h. Benzaldehyde (0.15 g, 1.4 mmol) was added to the mixture and the reaction was let stir for 30 mm followed by addition of sodium dithionite (0.65g. 3.8 mmoi). After 12 hat 100 C the reaction was cooled, diluted with EtOAc (50mL), and washed with H20 (25 mL x 3). The organic layer was dried (Na2504) and concentrated in vaeuo. Purification FCC. Si02, EtOAc/hexanes) afforded the title compound (0.10 g, 22%). MS (ESfl: mass caicd. for C,9H, ,FN4OS, 362.1; miz found, 363.1 [M+Hf. ?H NMR (400 MHz, DMSO-d6) oe 12.19 (br s, 11-I), 8.39 (dd, ,j:::: 8.5, 7.2 Hz. ifI). 7.79 (d, J::: 2.1 Hz, IH), 7.60 7.53 (m, 21-I), 7.48 — 7.37 (m. 31:1), 7.31 (dd, J: 8.4. 2.1 Fiz, 11-I), 7.24 (d, ,j:::: 8.4 Hz, IH), 7,14 (dd, J::::8.5.0.8Hz, 11-I).

56354-98-4 6-Aminobenzo[d]thiazol-2(3H)-one 6453329, athiazole compound, is more and more widely used in various.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
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3364-80-5, Thiazole-4-carboxaldehyde is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[623] Example 158 – 3-ri-Methyl-5-(4-methyl-cvclohexyl)-l,2,3,6-tetrahydro-pyridin-4-yl1-5-r4-; [624] A mixture of 4-bromobenzyl bromide (1.00 g, 4.00 mmol) and triphenylphosphine (1.70 g, 6.00 mmol) in toluene (10 mL) was stirred at 80 ¡ãC overnight. The reaction mixture wasconcentrated, followed by sonication in hexane, filtration, and a subsequent hexane wash gave a white solid, which was dried in vacuo. This white solid (906 mg, 1.77 mmol) was dissolved in THF (10 mL), cooled to 0 ¡ãC, and lithium hexamethyl disilazide (1 M) in THF (1.95 mL, 1.95 mmol) was added. After 0.5 hr, thiazole-4-carboxaldehyde (200 mg, 1.77 mmol) was added, the ice bath was removed, and the mixture stirred for 0.5 hr. The reaction mixture was quenched by the addition of water, extracted with EtOAc (2×30 mL), the organic layer was washed with brine, dried over MgS04, concentrated and filtered through a silica plug using 30percent -100percent EtOAc/hexane to give 158A as a clear oil. MS calcd: M+H)+ = 267. + = 267.

3364-80-5 Thiazole-4-carboxaldehyde 2763214, athiazole compound, is more and more widely used in various.

Reference£º
Patent; COCRYSTAL DISCOVERY, INC.; LEE, Sam, Sk; SHEN, Wang; ZHENG, Xiaoliang; JACOBSON, Irina, C.; WO2012/83105; (2012); A1;,
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35272-15-2, 2-Methylthiazole-4-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 32lambda/-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide 2-Methyl-1 ,3-thiazole-4-carboxylic acid (4.59g) (available from Maybridge), HATU (13.41g) and DIPEA (16.80ml) were stirred in DMF (140ml) for 30min at 2O0C. 6-Bromo- 1 H-indazol-4-amine (3.4g) (available from Sinova) was added and the reaction stirred at 2O0C for 2 days. The solvent was reduced to ~40ml and the reaction mixture was applied across 5×70 g aminopropyl SPE cartridges and left to stand for 3h. The cartridges were eluted with DCM:methanol (1 :1 ) and the combined solvent was evaporated in vacuo. The residue was suspended in DCM:methanol, adsorbed onto Florisil.(R). and purified by chromatography on silica gel (10Og cartridge) eluting with 0 – 15percent gradient of methanol (containing 1percent triethylamine) in DCM over 60min to give title compound (1.02g). LC/MS Rt 0.95min m/z 337 [MH+]. Method B

35272-15-2 2-Methylthiazole-4-carboxylic acid 284728, athiazole compound, is more and more widely used in various.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13750-63-5,(4-Methylthiazol-2-yl)methanol,as a common compound, the synthetic route is as follows.

Preparation 37; 2-Bromomethyl-5-chloro-thiopheneCool (5-chloro-thiophen-2-yl)-methanol (Preparation 30) (330 mg, 2.22 mmol) to 0 0C and add acetyl bromide (709 mg, 430 muL, 5.76 mmol). Allow to warm to room temperature over 18 h, dilute with EtOAc (10 mL), and cautiously add saturated aqueous NaHCO3 (3 mL). When the carbon dioxide evolution stops, load the mixture onto a Varian Chem Elut CE1005 solid phase extraction cartridge (Varian part number 12198006). Elute with EtOAc, collect, and concentrate about 50 mL to obtain the crude product. Purify on silica gel (12 g) using 0-15% EtOAc/hexanes to afford 250 mg (53%) of the title compound as a yellow oil. MS (EI): 210,212; 1H NMR (CDCl3): delta 6.92 (d, IH, /=3.5 Hz), 6.78 (d, IH, /=4.0 Hz), 4.66 (s, 2H).

13750-63-5 (4-Methylthiazol-2-yl)methanol 17750909, athiazole compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.45865-42-7,5-(tert-Butyl)-4-methylthiazol-2-amine,as a common compound, the synthetic route is as follows.

A mixture of 5-tert-butyl-4-methylthiazole-2-ylamine (1.5 g, 8.8 mmol) and 2-bromoethyl methyl ether (0.91 mL, 9.7 mmol) was warmed to 85 0C and allowed to stir for 24 hours. The crude material was dissolved in ~5 mL of a 1 :1 mixture OfCH2Cl2 and CH3OH and a small amount of silica gel was added. This mixture was concentrated to dryness and the residue was purified via flash column chromatography (SiO2, 9:1 :0.1 CH2Cl2 :CH3OH:NH4OH) to afford the title compound (1.0 g, 4.4 mmol, 50% yield). 1H NMR (300 MHz, CD3OD) delta ppm 1.41 (s, 9 H) 2.38 (s, 3 H) 3.35 (s, 3 H) 3.66 (t, J=4.70 Hz, 2 H) 4.16 (t, J=4.70 Hz, 2 H); MS (DCI/NH3) m/z 229 (M+H)+

45865-42-7 5-(tert-Butyl)-4-methylthiazol-2-amine 1081536, athiazole compound, is more and more widely used in various.

Reference£º
Patent; ABBOTT LABORATORIES; WO2009/67613; (2009); A1;,
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14527-41-4, 5-Thiazolecarboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 131VStep 1. Thiazole-5-carboxylic acid methoxy-methyl-amide (155)[0373] Thiazole-5-carboxylic acid (2g, 15.48mmol), HBTU (14g, 38.8mmol), and DIEA (16mL, 92.88mmol) were dissolved in DMF (5OmL) and stirred at rt until all starting material had been consumed. O,N-Dimethyl-hydroxy1amine (6g, 61.92mmol) was then added to the reaction mixture and stirred for 16 hours. The reaction was then evaporated to dryness, and purified on silica gel to produce compound 155 (1.7g, 65% yield). H1-NMR (DMSO d6): 9.30 (m, 1H), 8.50 (m, 1H), 3.76 (m, 3H), 3.30 (m, 3H).

14527-41-4 5-Thiazolecarboxylic acid 84494, athiazole compound, is more and more widely used in various.

Reference£º
Patent; GENELABS TECHNOLOGIES, INC.; WO2006/76529; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.56354-98-4,6-Aminobenzo[d]thiazol-2(3H)-one,as a common compound, the synthetic route is as follows.

General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg 6-amino-1,3-benzothiazol-2(3H)-one (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.

56354-98-4 6-Aminobenzo[d]thiazol-2(3H)-one 6453329, athiazole compound, is more and more widely used in various.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; WORTMANN, Lars; KETTSCHAU, Georg; PUeHLER, Florian; LIENAU, Philip; PETERSEN, Kirstin; HAeGEBARTH, Andrea; SUeLZLE, Detlev; WO2014/44691; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3364-80-5,Thiazole-4-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: A solution of substituted o-phenyldiamine (1.0 equiv), thiazole-4-aldehyde or pyridine-2-aldehyde (1.0 equiv) with sodium pyrosulfite in DMF was stirred at 120¡ã C overnight. On completion of the reaction monitored by TLC, the solvent was evaporated and the residue was purified by silica gel chromatography by DCM/MeOH system to afford the final product. If necessary, the crudeproduct could be recrystallized in DCM or dichloroethane to afford pure sample.

3364-80-5 Thiazole-4-carboxaldehyde 2763214, athiazole compound, is more and more widely used in various.

Reference£º
Article; Zhang, Chao; Zhong, Bo; Yang, Simin; Pan, Liangkun; Yu, Siwang; Li, Zhongjun; Li, Shuchun; Su, Bin; Meng, Xiangbao; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3774 – 3780;,
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2516-40-7, 2-Bromobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) imidazo [1,2- a] pyridine 200 mg, 0.580 mmol) was added Palladium acetate (6 mg, 0.03 mmol),Triphenylphosphine (30 mg, 0.12 mmol),Sodium carbonate (124 mg, 1.16 mmol) was added, Dioxane and water in a ratio of 1: 1 in an amount of 5 mL,2-Bromobenzothiazole (124 mg, 0.580 mmol) was added,Stir at 90 ¡ã C under nitrogen gas.After the reaction is completed, the reaction mixture is cooled to room temperature. The reaction mixture is separated into water and ethyl acetate, and the extracted organic layers are combined and washed with water. After drying with magnesium sulfate, the mixture was concentrated and the concentrate was purified by silica gel column chromatography (dichloromethane: ethyl acetate, 20: 1 v / v)To obtain 2- (3- (benzothiazol-2-yl) phenyl) -8-cyanoimidazo [1,2-a] pyridine (98 mg, 59percent).

2516-40-7 2-Bromobenzothiazole 612040, athiazole compound, is more and more widely used in various.

Reference£º
Patent; Korea Research Institute of Chemical Technology; Jeon Mun-guk; Kim Gwang-rok; Huh Yun-jeong; Lee Jun-mi; (27 pag.)KR2018/101671; (2018); A;,
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103261-70-7, Ethyl benzo[d]thiazole-5-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Aldehyde preparation: To a solution of 4-chloro-3-nitrobeznoic acid (20 g, 99.2 mmol, 1.0 eq) in dimethylformamide (400 mL) was added potassium carbonate (35 g, 254 mmol, 2.55 eq). The mixture was stirred 30 min and ethyl iodide (18.6 g, 119 mmol, 1.20 eq) was added. The reaction mixture was stirred at 50 [C] for 4h. Water (3 L) was added and the mixture was extracted with diethyl ether (2 x 500 mL). The organic extracts were combined, washed with brine (1 L), dried over anhydrous sodium sulfate and concentrated. The residue was crystallized from hexanes to provide 19.7 g (86%) of the ester. Data [: IH] NMR (500 MHz, CDC13) [8] 8.51 (d, 1H), 8.17 (dd, 1H), 7.65 (d, 1H), 4.43 (q, 2H), 1.42 (t, 3H). Sulfur (1.60 g, 49.9 mmol, 0.58 eq) was dissolved in a solution of sodium sulfide [NONAHYDRATE] (12.0 g, 50.0 mmol, 0.58 eq) in water (60 [ML).] This solution was combined with a solution of ethyl 4-chloro-3-nitrobenzoate (19.6 g, 85.4 mmol, 1.00 eq) in ethanol (100 mL). The resulting mixture was heated at reflux for 3 h. The hot reaction mixture was poured into water (600 mL) and stirred for 15 min. The product was isolated by filtration and recrystallized from ethanol to provide 16.45 g (77%) of the disulfide. Data: [‘H NMR] (500 MHz, CDC13) [5] 8.96 (d, 1H), 8.19 (dd, 1H), 7.88 (d, 1H), 4.43 (q, 2H), 1.41 (t, 3H). A mixture of diethyl 4,4’-dithiobis (3-nitrobenzoate) (11.2 g, 24.75 mmol, 1.00 eq) and zinc granules (15.0 g, 234 mmol, 9.47 eq) in formic acid (600 mL) was heated to reflux for 48 h. The mixture was cooled to room temperature and concentrated to dryness on vacuum rotary evaporator. The residue was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (500 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated on vacuum rotary evaporator. The residue was purified by chromatography on neutral Alumina (1/0 to 0/1 hexanes/dichloromethane) to provide 5.30 g (51%) of the benzthiazole ester. Data: 1H NMR (500 MHz, [CDC13)] [8] [9. 08 (S, 1H),] 8.83 (d, 1H), 8.14 (dd, 1H), 8.02 (d, 1H), 4.45 (q, 2H), 1.44 (t, 3H); MS [(EI)] m/z 208 [(M++1).] Diisobutylaluminum hydride (1.0 M in dichloromethane, 6.0 mL, 6 mmol, 1.05 eq) was added over 15 min to a solution of the ester (1.18 g, 5.70 mmol) in dichloromethane (40 mL) [AT-35] [C.] The reaction mixture was allowed to warm to rt and was maintained overnight. Analysis of the reaction progress by thin layer chromatography revealed the presence of starting material. The reaction mixture was cooled to [0 C] and was treated with additional diisobutylaluminum hydride (6.0 mL, 6 mmol). After 4 h at rt, the reaction was quenched by the addition of water (10 mL) and the slurry was poured onto 5% sodium hydroxide and dichloromethane (200 mL) and maintained for 30 min with vigorous stirring. The organic layer was separated, washed with brine, dried (sodium sulfate), and concentrated. The residue was dissolved in dichloromethane (100 mL) and was treated with manganese [(IV)] oxide (3.0 g) and powdered [4A] seives (3.0 g). The reaction mixture was filtered through Celite (100 mL dichloromethane rinse) after 14 h and the filtrate was extracted with 0.6 N aqueous sodium hydrogen sulite (2 x 150 mL). The combined aqueous layers were back-extracted with dichloromethane [(50] mL), were made basic (pH 11) by the addition of 50% sodium hydroxide, and were extracted with ethyl acetate (2 x 100 mL). The ethyl acetate layers were dried (sodium sulfate) and concentrated to provide 268 mg (29%) of the aldehyde as a tan solid. Data [: IHNMR (CDCL3) 6] 10.18 (s, 1H), 9.13 (s, [1H),] 8.61 (d, J= 1.0, 1H), 8.11 (d, J= 8.0, 1H), 8.01 (dd, J= 8.5, 1.5, 1H). Condensation: According to procedure A. Data: Yield: 86%. 1H NMR (CD30D) 8 8.97 (s, 1H), 8.75 (s, [1H),] 8.60 (s, [1H),] 8.06 (d, [J=] 0.6, [1H),] 7. 87 (d, [J=] 8.4, [1H),] 7.82 (dt, Jd = 7.8, Jt = 1. 8, 1H), 7.30 (dd, J= 7.8, 4.8, 1H), 7.26 (dd, J= 8.4, 1.6, 1H), 6.76 (s, 1H), 3.86 (t, J= 5.5, 2H), 2.85 (m, 2H), 1.79 (m, 2H); MS [(EL)] m/z 306 [(M+ +] 1).

The synthetic route of 103261-70-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2004/19943; (2004); A1;,
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