Heterocyclic Building Blocks-Thiazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24295-03-2,2-Acetylthiazole,as a common compound, the synthetic route is as follows.

In a 50 ml round bottom flask, 8 ml of anhydrous diethyl ether and 0.311 ml (2.2 mmol) of diisopropylamine were added and the solution was cooled to -60C.Then, 2.5 N n-hexane solution of BuLi (2.2 mmol) was added dropwise to the upper reaction system, and the reaction system was warmed to 0 C. and stirred for 15 minutes. Then, sclareolide(500 mg, 2.0 mmol) was added dropwise thereto at -60 C. Ether solution,The reaction mixture was stirred for a further 40 min and then a solution of 2-acetylthiazole (254.3 mg, 2.0 mmol) in diethyl ether was added dropwise to the upper reaction system. The reaction system is stirred at this temperature for 50 min and quenched with water.The organic layer was separated, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give CYL-2-QX-3A in a yield of 60.0%.

24295-03-2, The synthetic route of 24295-03-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sichuan China National Tobacco Industry Co., Ltd.; Chongqing China National Tobacco Industry Co., Ltd.; Tao Feiyan; Yang Wenmin; Feng Guanglin; Dai Ya; Li Chaorong; Ding Wei; Wang Yao; Zhou Sheng; Zhou Zhigang; Qiu Guangming; Liu Rucan; Zhang Ting; (11 pag.)CN105061418; (2017); B;,
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.1747-60-0,2-Amino-6-methoxybenzothiazole,as a common compound, the synthetic route is as follows.

The starting material 2-bromo-6-methoxy-benzothiazole is prepared by using a PEG- assisted Sandmeyer reaction of the commercially available 2-amino-6-methoxy- benzothiazole according to a literature procedure (N. Suzuki et al., Chemistry Express 1992, 7, 717).

1747-60-0, As the paragraph descriping shows that 1747-60-0 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; WO2008/89933; (2008); A2;,
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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.170961-15-6,tert-Butyl thiazol-2-ylcarbamate,as a common compound, the synthetic route is as follows.

General procedure: n-BuLi (2.5M in THF, 1.4equiv) was added drop wise to a mixture of compound 1a or 1b (1equiv) and aldehyde (1.2equiv) in THF (?20mL) at -78C for 2h. The reaction was quenched by adding a saturated aqueous solution of NH4Cl, extracted with EtOAc, washed with water and then brine. The organic phase was dried over anhydrous Na2SO4, evaporated, and the residue was purified by silica gel column chromatography, 170961-15-6

The synthetic route of 170961-15-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Khalil, Ahmed; Edwards, Jessica A.; Rappleye, Chad A.; Tjarks, Werner; Bioorganic and Medicinal Chemistry; vol. 23; 3; (2015); p. 532 – 547;,
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42182-65-0, Benzo[d]thiazol-2-ylmethanamine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of (4-chloro-6-methylpyrimidin-2-yl)aminosulfonyl chloride (8) (1 mmol), benzoxazol-2-amine (2a)/benzothiazol-2-amine (2b)/1H-benzimidazol-2-amine (2c)/(benzoxazol-2-yl) methanamine (3a)/(benzothiazol-2-yl)methanamine (3b)/(1H-benzimidazol-2-yl)methanamine (3c), (2.2 mmol), dry ethanol (8 ml) and acatalytic amount of methanesulfonic acid (0.4 ml) wererefluxed for 3-5 h. The contents of the flask were cooledand diluted with water (25 ml). The separated solid wasfiltered, washed with water, dried and recrystallized from 2-propanol.

42182-65-0, 42182-65-0 Benzo[d]thiazol-2-ylmethanamine 350414, athiazole compound, is more and more widely used in various.

Reference£º
Article; Seenaiah, Dandu; Rekha, Tamatam; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 2; (2017); p. 431 – 441;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.399-74-6,2-Chloro-6-fluorobenzo[d]thiazole,as a common compound, the synthetic route is as follows.

General procedure: Examples 103 and 104: N-i4,4-Difluoro-2-r(6-fluoro-l,3-benzothiazol-2- yl)amino]cyclopentyl}-2-(2 -l,2,3-triazol-2-yl)benzamide To a solution of N-(2-amino-4,4-difluorocyclopentyl)-2-(2H-l,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 28; 120 mg, 0.349 mmol) in dry DMSO (1.2 ml) was added 2-chloro-6-fluoro-l,3-benzothiazole (CAS number 399-74-6; 72 mg, 0.384 mmol) and DIPEA (183 mu, 1.047 mmol). The reaction was sealed and stirred at 140 C in a sand bath for 17 hours. The reaction was partitioned between ethyl acetate and water, washing with water, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was then purified by column chromatography (basic silica, 0-100 % ethyl acetate / petrol). The racemic mixture was then purified by SFC to give two enantiomers (Enantiomer 1/Example 103 and Enantiomer 2/Example 104) of the title compound.Example 103 (Enantiomer 1)1H NMR (400 MHz, OCM-d2) delta ppm 2.02 – 2.28 (m, 2 H), 2.72 – 2.98 (m, 2 H), 4.19 – 4.43 (m, 2 H), 6.91 – 7.14 (m, 1 H), 7.20 – 7.35 (m, 3 H), 7.36 – 7.42 (m, 1 H), 7.44 – 7.51 (m, 1 H), 7.52 – 7.60 (m, 1 H), 7.67 (s, 2 H), 7.74 – 7.84 (m, 1 H) MS ES+: 459Example 104 (Enantiomer 2)1H NMR (400 MHz, OCM-d2) delta ppm 2.02 – 2.28 (m, 2 H), 2.72 – 2.98 (m, 2 H), 4.19 – 4.43 (m, 2 H), 6.91 – 7.14 (m, 1 H), 7.20 – 7.35 (m, 3 H), 7.36 – 7.42 (m, 1 H), 7.44 – 7.51 (m, 1 H), 7.52 – 7.60 (m, 1 H), 7.67 (s, 2 H), 7.74 – 7.84 (m, 1 H)MS ES+: 459, 399-74-6

399-74-6 2-Chloro-6-fluorobenzo[d]thiazole 2049870, athiazole compound, is more and more widely used in various.

Reference£º
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.71574-33-9,4,5-Dimethylthiazol-2-amine hydrochloride,as a common compound, the synthetic route is as follows.,71574-33-9

To a solution of (9S)-2-(2-methylpyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine (600 mg, 2.253 mmol) in THF (15 mL) were added triethylamine (0.942 mL, 6.76 mmol) and triphosgene (334 mg, 1.126 mmol) at 30 C. and stirred for 1 h. Then 4,5-dimethylthiazol-2-amine hydrochloride (556 mg, 3.38 mmol) was added at 30 C. and reaction was heated at 70 C. for 16 h. The solvent evaporated under reduced pressure, residue diluted with water (40 ml) and extracted with DCM (2¡Á40 ml). The combined organic layer was washed with water, brine, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain crude compound. The crude mixture was purified by flash column chromatography and prep HPLC to afford (9S)-N-(4,5-dimethylthiazol-2-yl)-2-(2-methylpyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide (275 mg, 0.655 mmol, 42% yield) as a pale yellow solid (TLC: 10% MeOH in EtOAc, Rf: 0.3), LCMS (m/z): 421.27 [M+H]+. 1H NMR (400 MHz, CDCl3): delta ppm 14.79 (s, 2H), 8.64 (d, J=5.26 Hz, 2H), 8.02 (s, 1H), 7.64 (dd, J=5.26, 1.53 Hz, 1H), 7.54 (q, J=8.11 Hz, 1H), 4.99 (s, 1H), 3.42-3.18 (m, 3H), 3.12-2.89 (m, 1H), 2.79 (s, 3H), 2.28 (s, 3H), 2.22 (s, 3H), 2.00-1.75 (m, 1H), 1.52-1.35 (m, 2H).

The synthetic route of 71574-33-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); 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.72054-60-5,Ethyl 2-amino-5-methylthiazole-4-carboxylate,as a common compound, the synthetic route is as follows.,72054-60-5

General procedure: The solution of acid [11(a-d), 12b] (0.5mmol) and O-(benzotriazol-1-yl)-N,N,N?,N’- tetramethyluronium hexafluorophosphate (0.54mmol) in dry dichloromethane (10mL) and dimethyl aminopyridine (0.1mmol) was added to substituted thiazol-2-amine [2(a-c), 4, or 6] (0.5mmol) at 0C. The reaction mixture was stirred at room temperature for 16-20h. Later the reaction was quenched with water (5.0mL), extracted with dichloromethane (10.0mL¡Á2), and evaporated under reduced pressure. The residue was subjected to silica gel chromatography to give compound [(13a-13o) and (14a-14e)] in good yields

The synthetic route of 72054-60-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Guggilapu, Sravanthi Devi; Guntuku, Lalita; Reddy, T. Srinivasa; Nagarsenkar, Atulya; Sigalapalli, Dilep Kumar; Naidu; Bhargava, Suresh K.; Bathini, Nagendra Babu; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 83 – 95;,
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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.7210-73-3,Ethyl 4-methylthiazole-2-carboxylate,as a common compound, the synthetic route is as follows.,7210-73-3

A solution of ethyl 4-methyl-1 ,3-thiazole-2-carboxylate (1120) (208 mg, 1.215 mmol) in ethanol (6.028 ml) was stirred at room temperature under an atmosphere of argon. Hydrazine (0.046 ml, 1.458 mmol) was added and the solution was heated to reflux for 18 hours. The solution was cooled to room temperature and then the solvent was removed under reduced pressure to give a pale yellow coloured solid of desired product in 115 mg. LCMS m/z 157.92 [M+H] (at) 0.41 min (2 min run).

The synthetic route of 7210-73-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
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Thiazole | chemical compound | Britannica

7210-77-7, Ethyl 2,4-dimethylthiazole-5-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7210-77-7

Example 21 Preparation of 2,4-dimethylthiazole-5-methanol To a suspension of lithium aluminum hydride (563 mg, 14.8 mmol) in diethyl ether (25 mL) at 0 C. was added ethyl-2,4-dimethylthiazole-5-carboxylate (2.5 g, 13.5 mmol) in three portions. The reaction mixture was allowed to stir at 0 C. for 10 min, then at room temperature for 24 h. Ethyl acetate (65 mL) was added very slowly dropwise at 0 C. The reaction mixture was then added slowly to an aqueous solution of potassium sodium tartrate (30% w/v; 20 mL) and stirred for 2 h. The layers were separated and the aqueous layer was re-extracted with ethyl acetate (1*30 mL). The combined organic layers were dried (MgSO4), filtered, evaporated under reduced pressure. The resulting colorless solid was dried under high vacuum to give 2,4-dimethylthiazole-5-methanol (1.7 g, 91% yield). This material was used in a subsequent step without further purification.

The synthetic route of 7210-77-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Fotouhi, Nader; Gillespie, Paul; Guthrie, Robert William; Pietranico-Cole, Sherrie Lynn; Yun, Weiya; US2002/161237; (2002); A1;,
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7238-61-1, 2-Bromo-4-methylthiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7238-61-1

General procedure: (Scheme 1, Method C) 4-aminobenzenesulfonamide (4) (1.00 g, 5.81 mmol), 2- hydroxy-3-methoxybenzaldehyde (1.00 g, 7.00 mmol) in EtOH (29 mL) was heated to reflux for 4 h until reaction is an orange turbid mixture. The reaction mixture was cooled to room temperature before sodium borohydride (0.33 g, 8.71 mmol) was added and stirred for an additional 30 min. A white solid forms after 30 min and is collected by filtration and washed with copious amounts of ethanol, dried under vacuum and used as is in subsequent reactions. 1H NMR (400 MHz, DMSO- d6) delta 7.60-7.27 (m, 2H), 6.75-6.40 (m, 4H), 6.06 (t, J= 7.63 Hz, 1H), 4.18 (s, 2H), and 3.65 (s, 3H); 13C NMR (101 MHz, DMSO) delta 40.37, 55.32, 108.91, 109.42, 109.55, 111.29, 111.40, 121.05, 125.05, 127.49, 129.92, 150.17, 152.36, and 156.94; LC-MS retention time (Method 1): 2.876 min. General procedure: (Step iv) 4-(2-hydroxy-3-methoxybenzylamino)benzenesulfonamide (5) (0.58 mmol), arylbromide (0.70 mmol), K2CO3 (1.45 mmol), N,N’-dimethylethylenediamine (0.29 mmol), and copper(I)iodide (0.03 mmol) in 1,4-dioxane (1.5 mL) were place under N2 and sealed in a 5 mL sealed tube. The reaction was heated to 70 C for 6 to 8 h and monitored by LC/MS analysis. Upon completion the heterogeneous mixture was cooled to room temperature, filtered, and washed with dioxane. The solution was passed through a thiol cartridge (metal scavenging), diluted with AcOEt and washed with NH4CI (2X), water, and brine. The crude material was purified using a prep-HPLC (gradient 10-100% acetonitrile w/ 0.1% TFA in water w/ 0.1% TFA) to give the desired product. 4-(2-hydroxy-3-methoxybenzylamino)- V-(4-methylthiazol-2-yl)benzenesulfonamide TFA (40): Method C: using 2-bromo-4-methylthiazole; 1H NMR (400 MHz, DMSO-<) delta 12.31 (s, 1 H), 8.70 (s, 1 H), 7.48-7.32 (m, 3 H), 6.89-6.72 (m, 6 H), 6.61-6.47 (m, 3 H), 6.27 (s, 1 H), 4.20 (d, J= 5.90 Hz, 2 H), 3.76 (s, 3 H), and 1.95 (s, 3 H); LC-MS retention time (Method 1): 1.962 min; HRMS: m/z (M+H)+ (Calculated for C18H20N3O4S2, 406.0890) found 406.0875. The synthetic route of 7238-61-1 has been constantly updated, and we look forward to future research findings. Reference£º
Patent; EASTERN VIRGINIA MEDICAL SCHOOL; MALONEY, David, J.; LUCI, Diane, K.; JADHAV, Ajit; HOLMAN, Theodore; NADLER, Jerry, L.; HOLINSTAT, Michael; TAYLOR-FISHWICK, David; SIMEONOV, Anton; YASGAR, Adam; WO2015/54662; (2015); A1;,
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