Category: Benzisoxazole

16263-54-0 A common heterocyclic compound, 16263-54-0,3,6-Dichlorobenzo[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.

To a solution of l-Boc-5-trifluoromethoxybenzimidazole-2-one (5 g, 15.7 mmol) in DMF (20 ml) was added 3,6-dichlorobenzoisoxazole (3.0 g, 15.7 mmol) and Cs2CO3 (11 g, 31.4 mmol). The suspension was heated to 15O0C in an oil bath and stirred overnight. The mixture was then cooled to room temperature, diluted with water (30 ml) and extracted with ethyl acetate (2×20 ml). The organic extracts were combined, dried over anhydrous Mg2SO4, and concentrated to dryness. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (4:1) as solvent system. Fractions containing earlier eluted product were combined and concentrated to obtain l-[3-(6-chloro)-benzisoxazoyl]-5- trifluoromethoxylbenzimidazole-2-one as a white solid. 1H NMR (DMSO, 500 MHz) delta 8.28 (d, J=9.0Hz, IH), 8.12 (s, IH), 7.74 (d, J=9.0Hz, IH), 7.54 (d, J=8.5, IH), 7.14 (d, J=8.5, IH), 7.13 (s, IH). Fractions containing later eluted product were combined and concentrated to obtain l-[3-(6-chloro)-benzisoxazoyl]-6-trifluoromethoxylbenzimidazole-2-one as a white solid. 1H NMR (DMSO, 500 MHz) delta 8.28 (d, J=9.0Hz, IH), 8.12 (s, IH), 7.74 (d, J=9.0Hz, IH), 7.66 (brs, IH), 7.54 (d, J=8.5, IH), 7.13 (brs, IH).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16263-54-0,3,6-Dichlorobenzo[d]isoxazole,its application will become more common.

Reference£º
Patent; MERCK & CO., INC.; WO2006/22954; (2006); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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. 651780-27-7

To a mixture of ethyl 6-bromobenzisoxazole-3-carboxylate (2.0 g, 7.4 mmol) and t- butyl 5-cyanoanthranilate (1.62 g, 7.4 mmol) in toluene (27 [ML)] is added NaH (1.5 g of a 60% mineral oil dispersion, 3.8 mmol) under N2. The reaction mixture is stirred overnight at rt. This mixture is diluted with aq 1 N [HCI,] extracted with EtOAc (0.2 L). The EtOAc solution is dried and concentrated to give Preparation Pb as a solid : 1H NMR (300 MHz, CDC13) [8] 12.8 (1H), 9.05 [(1H),] 8.38 (1H), 8.18 (1H), 7.92 (1H), 7.82 (1H), 7.61 [(1H),] [1.] 69 [(9H).]

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,its application will become more common.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18428; (2004); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-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. 36216-80-5

Method BA A mixture of benzo[d]isoxazol-3-amine and a sulfonyl chloride in pyridine (1 ml.) was stirred at room temperature for 16 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration or DCM extraction (2×1 ml.) and purified using silica gel column chromatography (EtOAc/petroleum benzine 40-60 C gradient) or preparative mass-directed HPLC to give the desired product. See Table B for reaction components and amounts used as well as purification conditions.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

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

A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-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. 36216-80-5

A solution of 1 ,2-benzisoxazol-3-amine (1.00 g; CASNo. 36216-80-5) and triethylamine (1.09 mL) in acetonitrile (5 mL) was added dropwise to at 0 0C solution of phenyl chloroformate (0.989 mL) in THF (20 mL). The reaction was stirred at 0 0C for 1 h and then allowed to warm to room temp overnight. The reaction was diluted with ethyl acetate and washed with 1 N HCI and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to give the crude product as a reddish brown solid. The solid was triturated with refluxing diisopropyl ether, cooled to room temp, and filtered to give the final product as a tan solid (1.22 g, 64%). m/z 255 (MH+).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

Reference£º
Patent; PFIZER INC.; WO2009/127948; (2009); A1;; ; Patent; PFIZER INC.; WO2009/127949; (2009); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 851768-35-9,5-Amino-3-methylbenzo[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. 851768-35-9

Synthesis of 3-chloro-2-methyl-N-(3-methyl-benzo[d]isoxazol-5-yl)- benzenesulfonamide, STX 874 (KRB01027):; To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (128 mg, 0.567 mmol) in dichloromethane (3 mL) was added pyridine (110 muL, 1.35 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-3-methyl-1, 2-benzisoxazole [26] (80 mg, 0.54 mmol) was added. The resulting mixture was stirred for 4 h at room temperature, then saturated NaHCO3 solution (8 mL) was added and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (88 mg, 48%), single spot at Rf 0.58 (1: 1 hexane: ethyl acetate). mp 162.8-163. 2C, HPLC purity 99+% (tR 2.26 min in 10% water- acetonitrile).’H NMR (CDC13) : 6 7.80 (1H, dd, J=7.9, 1.3 Hz), 7.55 (1H, dd, J=8. 1, 1.1 Hz), 7.38 (2H, m), 7.17 (1 H, t, J=8.1 Hz), 7.10 (1H, dd, J=8.8, 2.2 Hz), 6.72 (1H, s, N-lez 2.72 (3H, s), 2.50 (3H, s). LCMS: 320.00 (M-CH3). FAB-MS (MH+, C15H13ClN2O3S) : calcd 337.0413, found 337.0422.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851768-35-9,5-Amino-3-methylbenzo[d]isoxazole,its application will become more common.

Reference£º
Patent; STERIX LIMITED; WO2005/42513; (2005); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

89976-56-7 A common heterocyclic compound, 89976-56-7,5-Methylbenzo[d]isoxazol-3-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.

Benzoic isoxazol-3-bis(N,N-t-butoxycarbonyl)amine (122): To a solution of 121 (148 mg, 1 mmol) in DCM (2 mL) was added di-t-butyldicarbonate (546 mg, 2.5 mmol), DIEA (0.348 mL, 2 mmol), and DMAP (22.2 mg, 1 mmol) at O0C. The reaction was warmed up to RT and stirred for 4 hr and then diluted with ethyl acetate and treated with aqueous ammonium chloride to pH 6. The organic layer was separated and washed with brine and concentrated in vacuo. The residue purified by silica gel chromatography using 100% hexane as the eluent to yield 122 (347 mg, 100%), LC-MS (ESI) m/z 348.8.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89976-56-7,5-Methylbenzo[d]isoxazol-3-amine,its application will become more common.

Reference£º
Patent; DAIAMED, INC.; WO2006/108039; (2006); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

16263-54-0 A common heterocyclic compound, 16263-54-0,3,6-Dichlorobenzo[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.

5) Preparation 6-chloro-3-piperazinyl-benzisoxazole 3,6-dichlorobenzisoxazole (5.2g, 27.8 mmol), and anhydrous piperazine (24g, 278 mmol) are placed in an egg type flask and react at 120C for 24 hours. After completion of the reaction, 52 ml of an ice-water mixture is added for quenching the reaction. Further 15 ml of 50% NaOH solution is added to the reaction solution. The reaction solution is stirred for 5 minutes and extracted with dichloromethane (30ml*3). The dichloromethane layer is combined, washed with 20 ml of saturated saline, dried over anhydrous MgSO4, evaporated to dryness, and subjected to a separation on a column of alumina (200-300mesh), eluting with dichloromethane_methanol=100:1, to obtain 4.7g of 6-chloro-3-piperazinyl-benzisoxazole, with a yield of 71%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16263-54-0,3,6-Dichlorobenzo[d]isoxazole,its application will become more common.

Reference£º
Patent; Jiangsu Guohua Investment Co., Ltd; Shanghai Institute of Pharmaceutical Industry; EP2322520; (2011); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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. 828300-70-5

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

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,Benzo[d]isoxazol-6-amine,828300-70-5,its application will become more common.

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

A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-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. 36216-80-5

Example 149: N-(benzo[d]isoxazol-3-yl)-2,6-dimethoxybenzenesulfonamide 149 A solution of 2,6-dimethoxybenzene-1-sulfonyl chloride I111 (0.088 g, 0.37 mmol) and benzo[d]isoxazol-3-amine (0.050 g, 0.37 mmol) in pyridine (1 ml.) was irradiated in the microwave at 1 10 C for 2 hours, then at 120 C for 2 hours. The reaction mixture was loaded onto silica and purified by column chromatography (12g Si02 cartridge, 0-35 % EtOAc in petroleum benzine 40-60 C) to give the title compound (3.9 mg, 3.1 % yield) as a white solid. NMR (400 MHz, CDCIs) d 8.30 (s, 1H), 8.17 (dt, J = 1.04, 8.15 Hz, 1H), 7.55 – 7.47 (m, 1H), 7.47 – 7.34 (m, 2H), 7.34 – 7.28 (m,1H), 6.60 (d, J = 8.52 Hz, 2H), 3.91 (s, 6H). LCMS-B: rt 3.13 min, m/z = 334.8[M+H]+.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,Benzo[d]isoxazol-3-amine,36216-80-5,its application will become more common.

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

89976-56-7 A common heterocyclic compound, 89976-56-7,5-Methylbenzo[d]isoxazol-3-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 mixture of 5-methylbenzo[d]isoxazol-3-amine (1.48 g, 10 mmol, 1.0 eq.), B0C2O (6.54 g, 30 mmol, 3.0 eq.), DMAP (122 mg, 1.0 mmol, 0.1 eq.), TEA (4.2 mL, 30 mmol, 3.0eq.) in DCM (30 mL) was refluxed for 18 h. The mixture was washed with water (30 mL X 2), dried over anhydrous Na2SC>4 and concentrated. The residue was purified via flash chromatography (PE/EA/DCM = 1/20/1-1/7/1, v/v/v) to afford tert-butyl [(tert- butoxy)-N-(5-methylbenz (3.2 g, 92%).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5-Methylbenzo[d]isoxazol-3-amine,89976-56-7,its application will become more common.

Reference£º
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics