Category: 36216-80-5

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 34 2,6-DICHLORO-N-(3-BENZISOXAZOLYL)BENZAMIDE 3-Aminobenzisoxazole (2 gram), 2,6-dichlorobenzoylchloride (2 gram), and 50 ml. of toluene are heated at reflux for 16 hours. After evaporation of the solvent at reduced pressure, the resultant oily semi-solid is triturated with ether. The solid so formed is then washed with ether and water and constitutes the desired product.

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; Eli Lilly and Company; US4322429; (1982); A;,
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

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.

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; TARGACEPT, INC.; MAZUROV, Anatoly A.; MIAO, Lan; SHOWALTER, Todd; WO2013/28587; (2013); 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 77; (3R)-1-[2-(1,2-Benzisoxazol-3-ylamino)-2-oxoethyl]-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane chloride (Isomer 1); a) N-1,2-Benzisoxazol-3-yl-2-chloroacetamide; Benzo[d]isoxazol-3-amine (1 g) and cesium carbonate (2.429 g) in dry DMF (20 mL) was stirred at 23 C. whilst bromoacetyl chloride (0.624 mL) was added dropwise to the mixture. After stirring for 8 h, the reaction was poured into water (100 mL) and the mixture extracted with diethyl ether (2¡Á200 mL). The combined extracts were dried over magnesium sulfate and concentrated to dryness. The crude product was purified on silica gel using 40% ether isohexane. The subtitled compound was isolated as a colourless solid (0.5 g).m/e 210 [M+H]+ 1H NMR (400 MHz, DMSO) delta 11.45 (1H, s), 8.02 (1H, d), 7.72-7.63 (2H, m), 7.39 (1H, ddd), 4.47 (2H, s).

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; Ford, Rhonan; Mete, Antonio; Millichip, Ian; Teobald, Barry; US2010/113510; (2010); 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

36216-80-5, EXAMPLE 7 N-[2-(4-Morpholinyl)ethyl]-1,2-benzisoxazol-3-amine To a solution of 3-amino-1,2-benzisoxazole (3.5 g) in N,N-dimethylformamide (DMF) (100 ml) was added sodium hydride (0.8 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)morpholine (4.0 g) in DMF (50 ml) was added followed by heating to 120 C. for one hour. TLC (5% MeOH/DCM) analysis revealed the absence of starting material. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water, dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluding with 1.5-2.5% MeOH/DCM afforded the product (2.5 g), m.p. 79-80 C. ANALYSIS: Calculated for C13 H17 N3 O2: 63.14%C 6.93%H 16.99%N Found: 63.47%C 6.87%H 16.95%N

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; Hoechst-Roussel Pharmaceutical Incorporated; US5494908; (1996); A;,
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

Benzisoxazole-3-amine 2 (2.68 g, 20 mmol) was dissolved in water (25 ml) and concentrated HCl (12.5 ml) under vigorous stirring in an ice/water bath. A freshly prepared, ice-cold solution of NaNO2 (1.4 g, 20 mmol) in water (10 ml) was added drop wise to the reaction mixture by keeping the internal temperature between 0 to 5 C. After the completion of addition, the reaction mixture was stirred for an additional 10 min. A freshly prepared solution of sodium azide (1.3 g, 20 mmol) in water (10 ml) was added drop wise to the reaction mixture via an additional funnel while keeping the internal temperature of the reaction mixture below 5 C. Upon complete addition of the sodium azide solution, the reaction mixture was stirred for an additional 20-30 min at 0 C, followed by stirring at room temperature for another 3 h. The reaction mixture was extracted with ethyl acetate EtOAc (25 ml) three times. The combined organic layer was washed with water (25 ml) and brine (25 ml), dried over anhydrous sodium sulphate and concentrated under reduced pressure to get crude benzisoxazole-3-azide 3, which was purified by column chromatography over silica gel (60-120 mesh) using hexane/EtOAc (8:2) as eluent. The pure benzisoxazole-3-azide 3 was stored at 2-5 C in the refrigerator.

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
Article; Ashwini, Nanjundaswamy; Garg, Manoj; Mohan, Chakrabhavi Dhananjaya; Fuchs, Julian E.; Rangappa, Shobith; Anusha, Sebastian; Swaroop, Toreshettahally Ramesh; Rakesh, Kodagahalli S.; Kanojia, Deepika; Madan, Vikas; Bender, Andreas; Koeffler, H. Phillip; Basappa; Rangappa, Kanchugarakoppal S.; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6157 – 6165;,
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 77; (3R)-1-[2-(1,2-Benzisoxazol-3-ylamino)-2-oxoethyl]-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane chloride (Isomer 1); a) N-1,2-Benzisoxazol-3-yl-2-chloroacetamide; Benzo[d]isoxazol-3-amine (1 g) and cesium carbonate (2.429 g) in dry DMF (20 mL) was stirred at 23 C. whilst bromoacetyl chloride (0.624 mL) was added dropwise to the mixture. After stirring for 8 h, the reaction was poured into water (100 mL) and the mixture extracted with diethyl ether (2¡Á200 mL). The combined extracts were dried over magnesium sulfate and concentrated to dryness. The crude product was purified on silica gel using 40% ether isohexane. The subtitled compound was isolated as a colourless solid (0.5 g).m/e 210 [M+H]+ 1H NMR (400 MHz, DMSO) delta 11.45 (1H, s), 8.02 (1H, d), 7.72-7.63 (2H, m), 7.39 (1H, ddd), 4.47 (2H, s).

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; Ford, Rhonan; Mete, Antonio; Millichip, Ian; Teobald, Barry; US2010/113510; (2010); 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

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,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 mixture of benzo[d]isoxazol-3-ylamine (3.0 g) and CICO2Ph (0.94 ml_) in dry CH3CN (30 ml_) was stirred for 23 h at 70 0C. The reaction mixture was poured into de- ionized water, stirred for 30 min and filtered. The isolated solid was rinsed thoroughly with water and then dried under high vacuum to give 1.90 g (100%) of the title compound. MS: 255.1.

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; JANSSEN PHARMACEUTICA N.V.; WO2008/153752; (2008); A2;,
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 27 1-(2,6-DICHLOROBENZOYL)-3-(3-BENZISOXAZOLYL)UREA 3-Aminobenzisoxazole (300 grams) and 2,6-dichlorobenzoyl isocyanate (600 grams) in 50 ml. methylene chloride were stirred at room temperature for one hour. The solvent was then evaporated and the precipitate recrystallized from ethanol. The identity of the product was determined by NMR and IR analysis, yield 500 mg., m.p.=212-215 C. Calculated: C, 51.45; H, 2.59; N, 12.00. Found: C, 51.35; H, 2.40; N, 11.84.

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; Eli Lilly and Company; US4336264; (1982); A;,
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

(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).

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