Category: 4576-90-3

Name is Isothiazole-3-carboxylic acid, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 4576-90-3, its synthesis route is as follows.

To a suspension of isothiazole-3-carboxylic acid (2 g, 15.49 mmol) in DCM at 0 C was added oxalyl dichloride (1.3 equiv.) followed by three drops of DMF. Bubbling commenced, and the reaction was warmed to 23 C after 10 min. The mixture was stirred for 3 h, then cooled to 0 C. N,0-dimethylhydroxylamine hydrochloride (1.3 equiv.) was added to the reaction, followed by triethylamine (3.5 equiv.) which was added dropwise via syringe over 10 min. Reactions was warm slowly to 23 C overnight, and stirred for a total of 15 h. Reaction mixture was diluted with IN HC1 solution and dichloromethane (1 :1 ratio). Layers were separated, and the aqueous layer was extracted with DCM (2x). Combined organic layers were dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Crude reside purified via silica gel chromatography (utilizing a hexane/ethyl acetate mix as eluent) to deliver the desired intermediate, N-methoxy-N-methylisothiazole-3-carboxamide (1 g, 38%> yield) as a pale yellow solid. NMR (400 MHz, CDCI3) delta ppm 8.67 (d, 1 H), 7.69 (br s, 1 H), 3.80 (s, 3 H), 3.46 (br s, 3 H).

4576-90-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,4576-90-3 ,Isothiazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; IRONWOOD PHARMACEUTICALS, INC.; BARDEN, Timothy Claude; SHEPPECK, James Edward; RENNIE, Glen Robert; RENHOWE, Paul Allan; PERL, Nicholas; NAKAI, Takashi; MERMERIAN, Ara; LEE, Thomas Wai-Ho; JUNG, Joon; JIA, James; IYER, Karthik; IYENGAR, Rajesh R.; IM, G-Yoon Jamie; (293 pag.)WO2016/44447; (2016); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

4576-90-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Isothiazole-3-carboxylic acid, cas is 4576-90-3,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Preparation of tert-butyl isothiazol-3-ylcarbamate To a slurry of isothiazole-3-carboxylic acid (5.0 g, 38.7 mmol) in tert-butanol (194 mL) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenylphosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 hours. Concentration under reduced pressure provided a residue which was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), 1 N sodium hydroxide solution (50 mL), water (100 mL), and brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated in vacuo. Purification of the residue by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79% yield): 1H NMR (300 MHz, CDCl3) delta 9.03-8.98 (m, 1H), 8.58 (d, J=4.9 Hz, 1H), 7.70 (d, J=4.9 Hz, 1H), 1.53 (d, J=0.7 Hz, 9H).

The chemical industry reduces the impact on the environment during synthesis,4576-90-3,Isothiazole-3-carboxylic acid,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Xenon Pharmaceuticals Inc.; Andrez, Jean-Christophe; Burford, Kristen Nicole; Dehnhardt, Christoph Martin; Focken, Thilo; Grimwood, Michael Edward; Jia, Qi; Lofstrand, Verner Alexander; Wesolowski, Steven Sigmund; Wilson, Michael Scott; US2020/71313; (2020); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

4576-90-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Isothiazole-3-carboxylic acid, cas is 4576-90-3,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

[00163] To a solution of isothiazole-3-carboxylic acid (20 mg, 0.15 mmol), EDC (32.4 mg, 0.17 mmol), HOBt (23. mg, 0.17 mmol) in DMF (0.3 mL) was added 3- amino-N-cyclopropyl-4-methyl-benzamide hydrochloride (35 mg, 0.15 mmol) followed by DIPEA (0.03 mL, 0.17 mmol). The reaction was heated at 500C for 1 h. Water (0.6 mL) was added dropwise and the reaction removed from heating. The solids were stirred overnight at room temp, filtered, and washed with water to give (42.1 mg, 91% yield). HPLC tR= 2.63 min, 99.80 % purity; LCMS 302.1 (M + H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Isothiazole-3-carboxylic acid, 4576-90-3

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/57775; (2008); A2;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

Isothiazole-3-carboxylic acid, cas is 4576-90-3, it is a common heterocyclic compound, the isothiazole compound, its synthesis route is as follows.,4576-90-3

EXAMPLE 277 Synthesis of (S)-4-((1-benzylpyrrolidin-3-yl)(methyl)amino)-2-fluoro-//-(isothiazol-3-yl)- 5-methylbenzenesulfonamide 2,2,2-trifluoroacetate Step 1. Preparation of te/f-butyl isothiazol-3-ylcarbamate To a slurry of isothiazole-3-carboxylic acid (5.0 g, 38.7 mmol) in terf-butanol (194 mL) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenylphosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 hours. Concentration under reduced pressure provided a residue which was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), 1 N sodium hydroxide solution (50 mL), water (100 mL), and brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated in vacuo. Purification of the residue by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79 % yield): H NMR (300 MHz, CDCI3) 9.03-8.98 (m, 1 H), 8.58 (d, J = 4.9 Hz, 1 H), 7.70 (d, J = 4.9 Hz, 1 H), 1.53 (d, J = 0.7 Hz, 9H).

With the rapid development of chemical substances, we look forward to future research findings about Isothiazole-3-carboxylic acid

Reference£º
Patent; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BURFORD, Kristen, Nicole; CHOWDHURY, Sultan; COHEN, Charles, Jay; DEHNHARDT, Christoph, Martin; DEVITA, Robert, Joseph; EMPFIELD, James, Roy; FOCKEN, Thilo; GRIMWOOD, Michael, Edward; HASAN, Syed, Abid; JOHNSON, James, Philip, Jr.; ZENOVA, Alla, Yurevna; (493 pag.)WO2017/201468; (2017); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

Isothiazole-3-carboxylic acid, cas is 4576-90-3, it is a common heterocyclic compound, the isothiazole compound, its synthesis route is as follows.,4576-90-3

[00163] To a solution of isothiazole-3-carboxylic acid (20 mg, 0.15 mmol), EDC (32.4 mg, 0.17 mmol), HOBt (23. mg, 0.17 mmol) in DMF (0.3 mL) was added 3- amino-N-cyclopropyl-4-methyl-benzamide hydrochloride (35 mg, 0.15 mmol) followed by DIPEA (0.03 mL, 0.17 mmol). The reaction was heated at 500C for 1 h. Water (0.6 mL) was added dropwise and the reaction removed from heating. The solids were stirred overnight at room temp, filtered, and washed with water to give (42.1 mg, 91% yield). HPLC tR= 2.63 min, 99.80 % purity; LCMS 302.1 (M + H).

With the rapid development of chemical substances, we look forward to future research findings about Isothiazole-3-carboxylic acid

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/57775; (2008); A2;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO80,mainly used in chemical industry, its synthesis route is as follows.,4576-90-3

To a solution of 500 mg (3.87 mmol) of isothiazol-3-carboxylic acid (Apollo Scientific), 415 mg (4.25 mmol) of N,O-dimethylhydroxylamine hydrochloride and 30 mg (0.196 mmol) of 1-hydroxybenzotriazole monohydrate in methylene chloride (20 ml) were added 2.7 mL (15.46 mmol) of diisopropylamine and 1.49 g (7.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide under an argon atmosphere, and the mixture was stirred at room temperature for 21 hours. After completion of the reaction, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine, subsequently dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate = 90:10 to 60:40 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 598 mg (3.47 mmol, yield 90%) of the title compound as a colorless oil Mass spectrum (EI, m/z): 172 [M]+. 1H-NMR spectrum (400 MHz, CDCl3) delta : 8.68 (1H, d, J = 4.6 Hz), 7.69 (1H, d, J = 4.0 Hz), 3.81 (3H, s), 3.47 (3H, brs).

With the complex challenges of chemical substances, we look forward to future research findings about Isothiazole-3-carboxylic acid,belong isothiazole compound

Reference£º
Patent; UBE Industries, Ltd.; IWASE, Noriaki; NISHIDA, Hiroshi; OKUDO, Makoto; ITO, Masaaki; KONO, Shigeyuki; MATOYAMA, Masaaki; USHIYAMA, Shigeru; OKANARI, Eiji; MATSUNAGA, Hirofumi; NISHIKAWA, Kenji; KIMURA, Tomio; EP2940013; (2015); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO116,mainly used in chemical industry, its synthesis route is as follows.,4576-90-3

To a slurry of isothiazole-3-carboxylic acid (5.0 g, 38.7 mmol) in terf-butanol (194 ml_) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenyl phosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 hours. After cooling the ambient temperature, the reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (300 ml_). The organic layer was washed with water (100 ml_), 1 N sodium hydroxide solution (50 ml_), water (100 ml_), brine (50 ml_), and dried over anhydrous magnesium sulfate. Filtration and concentration of the filtrate in vacuo afforded a residue. Purification of the residue by column (0805) chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79 % yield): 1FI NMR (300 MHz, CDCIs) 9.03-8.98 (m, 1 H), 8.58 (d, J = 4.9 Hz, 1 H), 7.70 (d, J = 4.9 Hz, 1 H), 1.53 (d, J = 0.7 Hz, 9H).

With the complex challenges of chemical substances, we look forward to future research findings about Isothiazole-3-carboxylic acid,belong isothiazole compound

Reference£º
Patent; XENON PHARMACEUTICALS INC.; FOCKEN, Thilo; ANDREZ, Jean-Christophe; BURFORD, Kristen Nicole; DEHNHARDT, Christoph Martin; GRIMWOOD, Michael Edward; JIA, Qi; LOFSTRAND, Verner Alexander; WILSON, Michael Scott; ZENOVA, Alla Yurevna; WESOLOWSKI, Steven Sigmund; SUN, Shaoyi; (205 pag.)WO2020/47323; (2020); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

Isothiazole-3-carboxylic acid, cas is 4576-90-3, it is a common heterocyclic compound, the isothiazole compound, its synthesis route is as follows.,4576-90-3

To a suspension of isothiazole-3-carboxylic acid (2 g, 15.49 mmol) in DCM at 0 C was added oxalyl dichloride (1.3 equiv.) followed by three drops of DMF. Bubbling commenced, and the reaction was warmed to 23 C after 10 min. The mixture was stirred for 3 h, then cooled to 0 C. N,0-dimethylhydroxylamine hydrochloride (1.3 equiv.) was added to the reaction, followed by triethylamine (3.5 equiv.) which was added dropwise via syringe over 10 min. Reactions was warm slowly to 23 C overnight, and stirred for a total of 15 h. Reaction mixture was diluted with IN HC1 solution and dichloromethane (1 :1 ratio). Layers were separated, and the aqueous layer was extracted with DCM (2x). Combined organic layers were dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Crude reside purified via silica gel chromatography (utilizing a hexane/ethyl acetate mix as eluent) to deliver the desired intermediate, N-methoxy-N-methylisothiazole-3-carboxamide (1 g, 38%> yield) as a pale yellow solid. NMR (400 MHz, CDCI3) delta ppm 8.67 (d, 1 H), 7.69 (br s, 1 H), 3.80 (s, 3 H), 3.46 (br s, 3 H).

As the rapid development of chemical substances, we look forward to future research findings about 4576-90-3

Reference£º
Patent; IRONWOOD PHARMACEUTICALS, INC.; BARDEN, Timothy Claude; SHEPPECK, James Edward; RENNIE, Glen Robert; RENHOWE, Paul Allan; PERL, Nicholas; NAKAI, Takashi; MERMERIAN, Ara; LEE, Thomas Wai-Ho; JUNG, Joon; JIA, James; IYER, Karthik; IYENGAR, Rajesh R.; IM, G-Yoon Jamie; (293 pag.)WO2016/44447; (2016); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4576-90-3,Isothiazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.,4576-90-3

To a slurry of isothiazole-3-carboxylic acid (5.0 g, 38.7 mmol) in terf-butanol (194 ml_) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenyl phosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 hours. After cooling the ambient temperature, the reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (300 ml_). The organic layer was washed with water (100 ml_), 1 N sodium hydroxide solution (50 ml_), water (100 ml_), brine (50 ml_), and dried over anhydrous magnesium sulfate. Filtration and concentration of the filtrate in vacuo afforded a residue. Purification of the residue by column (0805) chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79 % yield): 1FI NMR (300 MHz, CDCIs) 9.03-8.98 (m, 1 H), 8.58 (d, J = 4.9 Hz, 1 H), 7.70 (d, J = 4.9 Hz, 1 H), 1.53 (d, J = 0.7 Hz, 9H).

As the paragraph descriping shows that 4576-90-3 is playing an increasingly important role.

Reference£º
Patent; XENON PHARMACEUTICALS INC.; FOCKEN, Thilo; ANDREZ, Jean-Christophe; BURFORD, Kristen Nicole; DEHNHARDT, Christoph Martin; GRIMWOOD, Michael Edward; JIA, Qi; LOFSTRAND, Verner Alexander; WILSON, Michael Scott; ZENOVA, Alla Yurevna; WESOLOWSKI, Steven Sigmund; SUN, Shaoyi; (205 pag.)WO2020/47323; (2020); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

A common heterocyclic compound, the isothiazole compound, name is Isothiazole-3-carboxylic acid,cas is 4576-90-3, mainly used in chemical industry, its synthesis route is as follows.,4576-90-3

To a stirred suspension of isothiazole-3-carboxylic acid (10.02 g, 77.6 mmol) in anhydrous te/f-butanol (80 ml_) and anhydrous toluene (120 ml_) was slowly added triethylamine (13.0 ml_, 93.12 mmol). The mixture was stirred at ambient temperature for 5 minutes and then diphenyl phosphoryl azide (18.42 ml_, 85.36 mmol) was added dropwise to it. The reaction mixture was stirred at ambient temperature for 1 h, gradually warmed to 85 C over 1 h, and then heated at 85 C with stirring for 7 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (150 ml_) and saturated aqueous sodium bicarbonate (150 ml_). The layers were separated and the aqueous layer was extracted with ethyl acetate (2 c 100 ml_). The combined organic layers were washed with water (150 ml_), brine (150 ml_), dried over magnesium sulfate, and filtered. Concentration of the filtrate in vacuo provided a residue, which was purified by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane. Further purification by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in dichloromethane, afforded the title compound as a colorless solid (10.33 g, 66% yield): 1H NMR (400 MHz, CDCI3) d 8.56 (dd, J = 4.9, 0.6 Hz, 1 H), 8.11 (s, 1 H), 7.66 (d, J = 4.9 Hz, 1 H), 1.53 (s, 9H); MS (ES+) m/z 201.1 (M + 1).

As the rapid development of chemical substances, we look forward to future research findings about 4576-90-3

Reference£º
Patent; XENON PHARMACEUTICALS INC.; FOCKEN, Thilo; BURFORD, Kristen Nicole; LOFSTRAND, Verner Alexander; WILSON, Michael Scott; ZENOVA, Alla Yurevna; (121 pag.)WO2019/241533; (2019); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com