Heterocyclic Building Blocks-Benzisoxazole

239097-74-6,A common heterocyclic compound, 239097-74-6,Benzo[d]isoxazol-5-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a suspension of intermediate ester (105 mg, 0.340 mmol) in DMF (0.5 mL) was added a solution of 1,2-benoxazol-5-amine (46 mg, 0.340 mmol) in DMF (0.5 mL). The reaction mixture was stirred at room temperature for 2 hours until the reaction was complete, and quenched with the addition of TFA (5 drops). The precipitated solid was collected by filtration, suspended in DCM, basified with saturated NaHCO3 to pH ~8. The aqueous layer was extracted with DCM, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by trituration in DCM/Et2O, collected by filtration, and dried in vacuo to give the title compound (50 mg, 48%) as a yellow solid.1H NMR (400 MHz, CDCl3): delta 10.05 (s, 1H), 8.72 (s, 1H), 8.55 (s, 1H), 8.07 (s, 1H), 7.68 (dd, J = 6.8 Hz, 1.6 Hz, 1H), 7.59 (d, J = 6.8 Hz, 1H), 6.59 (s, 1H), 2.71 (s, 3H), 2.70 (s, 3H). LC-MS m/z: 308.1 [M+H+]. HPLC Purity (214 nm): 98%; tR = 8.38 min.

The chemical industry reduces the impact on the environment during synthesis, 239097-74-6,Benzo[d]isoxazol-5-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse Marie, Josee; (134 pag.)WO2016/73889; (2016); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 651780-27-7,651780-27-7

651780-27-7, A solution of ethyl 6-brom-1, 2-benzisoxazole-3-carboxylate (Intermediate 55) (0.05g) and cyclopropylamine (0. 03ml) in methanol (lml) was stirred at reflux for 6h. The solvent was evaporated and the residue was triturated with ether to give the title compound as a white solid (0.04g).

According to the analysis of related databases, 651780-27-7, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/10995; (2004); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, as follows.37924-85-9

General procedure: To NaOMe (25% soln, 0.5 mL, 2.2 mmol) in MeOH (5 mL) was added thiosemicarbazide 9 (200 mg, 2.2 mmol). Diethyloxalate (0.3 mL, 2.2 mmol) was then added dropwise. The mixture was heated at 65 C for 2 h and then cooled to rt. 1-(Bromomethyl)-4-chlorobenzene (500 mg, 2.4 mmol) was added in one portion; stirring was continued at rt for 3 h and then heated overnight at 50 C. The reaction mixture was concentrated. The residue was dissolved in EtOAc (40 mL), washed with water (20 mL), and brine (20 mL). The organic phase was dried over Na2SO4, concentrated and purified by silica gel column chromatography (EtOAc w/ 0.2% HOAc). The product was triturated in Et2O to afford 59 mg of 6g as a light yellow solid (10% yield)

According to the analysis of related databases, 3-(Bromomethyl)benzo[d]isoxazole, the application of this compound in the production field has become more and more popular.

Reference£º
Article; Hin, Niyada; Duvall, Bridget; Berry, James F.; Ferraris, Dana V.; Rais, Rana; Alt, Jesse; Rojas, Camilo; Slusher, Barbara S.; Tsukamoto, Takashi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2088 – 2091;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 36216-80-5,Benzo[d]isoxazol-3-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.36216-80-5

(2) Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate; To a solution of 1,2-benzisoxazol-3-amine (4.00 g, 29.8 mmol) and pyridine (7.25 ml, 89.6 mmol) in tetrahydrofuran (100 ml) was added under ice-cooling, 2,2,2-trichloroethyl chloroformate (8.20 ml, 59.6 mmol), and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 20 minutes. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the residue was added hexane to give 13.3 g (91.7%) of the desired product as a solid. 1H-NMR (CDCl3) delta; 4.82 (4H, s), 7.36 – 7.44 (1H, m), 7.59 – 7.65 (3H, m).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, Benzo[d]isoxazol-3-amine.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 719-64-2,5-Chloro-3-phenylbenzo[c]isoxazole, as follows.719-64-2

(2) Take 10.0g of intermediate (II) into a three-necked bottle.50ml ethanol, 4.8g iron powder,After refluxing for 0.5 h, 1 ml of sulfuric acid (6 mol/L) was added dropwise.After the completion of the dropwise addition, the reaction was refluxed for 1 h.After the reaction is completed, a NaOH solution is added to adjust the pH to 8,Cool down to 50 C, add 0.2g activated carbon,Reflux for 0.5h,Thermal filtration into the crystallization bottle, cooling and crystallization,Ethanol washing, drying to obtain intermediate (III) 9.60g, The yield is 95.1%.The melting point is 96.3-98.2 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-3-phenylbenzo[c]isoxazole, and friends who are interested can also refer to it.

Reference£º
Patent; Qilu Tianhe Huishi Pharmaceutical Co., Ltd.; Yuwen Li; Guan Qinghua; Zhao Xudong; Li Baoyong; (6 pag.)CN108250091; (2018); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

37924-85-9,Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3-(Bromomethyl)benzo[d]isoxazole,37924-85-9, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 18A mixture of 18a (20 mg, 0.060 mmol), 18b (12.7 mg, 0.060 mmol), and potassium carbonate (24.8 mg, 0.18 mmol) in DMF (1 ml) was heated at 50 C for 2h. The reaction solution was purified on RP-HPLC using 10-100% acetonitrile (0.05%TFA) to give 18 as the TFA salt.’HNMR (acetonitrile-d3, 500 MHz) delta = 8.047-8.031 (dd, J = 8.1Hz, IH), 7.738-7.723 (m, 2H), 7.503-7.452 (m, IH), 7.448 (s, IH), 7.399-7.321 (m, 5H), 7.067-7.052 (dd, J – 7.5Hz, IH), 6.173 (s, IH), 4.755 (s, 2H), 3.736-3.701(m, 2H), 3.550-3.450 (m, 2H), 2.800-2.745 (m5 IH), 2.4Gamma3- 2.404 (m, IH), 2.141-2.1 10 (m, IH), 2.036-2.001 (m IH); m z: calcd. for C26H22Cl2N202:465.37; found [M+H+]: 465.00; 466.94.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 37924-85-9.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DING, FA-Xiang; JIANG, Jinlong; SHEN, Dong-Ming; SHEN, Hong; SHI, Zhi-Cai; WO2011/137024; (2011); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

828300-70-5,A common heterocyclic compound, 828300-70-5,Benzo[d]isoxazol-6-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A quantity of 0.13 g (1 mmole) OF BENZO [d] isoxazol-6-ylamine is treated with 0.27 g (1 mmole) of 6, 8-Dibromo-imidazo [1, 2-a] pyrazine in acetonitrile with 3 eq. OF K2C03 AT REFLUX for 16 hrs. The reaction mixture is cooled partitioned between ethyl acetate and water, the organic extracts are dried over anhydrous MGSO4 and evaporated in vacuo to afford Benzo [d] ISOXAZOL-6-YL- (6-BROMO- imidazo [1, 2-A] PYRAZIN-8-YL)-AMINE, 828300-70-5

The chemical industry reduces the impact on the environment during synthesis, 828300-70-5,Benzo[d]isoxazol-6-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; CELLULAR GENOMICS, INC.; WO2005/5429; (2005); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

37924-85-9 A common heterocyclic compound, 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 1: To a -78 C solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[bl[1,4ldiazepin- 3-yl)-carbamic acid tert-butyl ester (807 mg, 2.91 mmol) in THF (19.4 mL) was added lithium bis(trimethylsilyl)amide (3.2 mL, 1.0 M solution in THF, 3.2 mmol), dropwise. The mixture was stirred at -78 C for 15 mm, then a mixture of Nal (523 mg, 3.49 mmol) and 3- (bromomethyl)benzo[dlisoxazole (740 mg, 3.49 mmol) in THF (9.7 mL) was added dropwise over 10 mm. The mixture was stirred at -78 C for 50 mm., warmed to RT and stirred for 4.5 h. The mixture was diluted with 1 N citric acid and extracted with EtOAc. The combined extractswere washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide a -4:1 mixture of (S)-tert-butyl 1-(benzo[dlisoxazol-3-ylmethyl)-2- oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1 ,4jdiazepin-3-ylcarbamate and (S)-tert-butyl 1- (benzo [djisoxazol-3 -ylmethyl)-4-oxo-2,3 ,4,5 -tetrahydro- 1 H-benzo [bI [1,41 diazepin-3-ylcarbamate (742 mg, 63 %) as a yellow foam. LC-MS mlz 431 [M+Naj.

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 37924-85-9 reaction routes.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Shaoqing; DONNELL, Andrew F.; KESTER, Robert Francis; LE, Kang; LOU, Yan; MICHOUD, Christophe; REMISZEWSKI, Stacy; RUPERT, Kenneth C.; WEISEL, Martin; WO2015/71393; (2015); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5,Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. Benzo[d]isoxazol-3-amine,36216-80-5, This compound has unique chemical properties. The synthetic route is as follows.

Example 148: N-(benzo[d]isoxazol-3-yl)-2,4-dimethoxybenzenesulfonamide 148 A solution of 2,4-dimethoxybenzenesulfonyl chloride (0.18 g, 0.75 mmol) and benzo[d]isoxazol-3-amine (0.10 g, 0.75 mmol) in pyridine (1 ml.) was irradiated in the microwave at 1 10 C for 2 hours. The resultant mixture was loaded onto silica gel and the product purified twice by column chromatography (4 g Si02 cartridge, 0-45% EtOAc in petroleum benzine 40-60 C then 4g Si02 cartridge, 0-35% EtOAc in petroleum benzine 40-60 C) to yield two batches (78 mg and 5 mg) of [183] the title compound (total mass 83 mg, 33 % yield) as white solids. 1H NMR (400 MHz, CDCI3) d 8.1 1 (d, J = 8.05 Hz, 1H), 7.79 (s, 1H), 7.70 (d, J = 8.81Hz, 1H), 7.57 – 7.50 (m, 1H), 7.47 – 7.40 (m, 1H), 7.37 – 7.29 (m, 1H), 6.50 (d, J = 2.27 Hz, 1H), 6.42 (dd, J = 2.25, 8.81Hz, 1H), 3.98 (s, 3H), 3.81 (s, 3H). LCMS-B: rt 3.20 min, m/z = 356.8 [M+Na]+, 334.8 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 36216-80-5.

Reference£º
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 36216-80-5,Benzo[d]isoxazol-3-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 36216-80-5,36216-80-5

1 ,2-Benzoxazol-3-amine (802 mg, 5.98 mmol) was dissolved in a mixture of anhydrous dichloromethane (4 ml_) and anhydrous pyridine (1 .5 ml_, 19 mmol). To this mixture was added, drop-wise, a solution of ethyl malonyl chloride (1.00 g, 6.64 mmol) in anhydrous dichloromethane (4 ml_). The resulting warm mixture (from slight exotherm) was stirred at ambient temperature for 30 min and quenched with the addition of cold water (20 ml_). Solid sodium carbonate was added until a pH of 10 was reached, and the mixture was stirred at ambient temperature for 1 hour. The organic layer was separated and the aqueous layer back-extracted withdichloromethane (4 x 30 ml_). The combined organic layers were passed through a phase separator column and concentrated under reduced pressured to yield crude ethyl 3-(1 ,2-benzoxazol-3-ylamino)-3- oxopropanoate.

According to the analysis of related databases, 36216-80-5, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; TARGACEPT, INC.; MAZUROV, Anatoly A.; MIAO, Lan; SHOWALTER, Todd; WO2013/28587; (2013); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics