Tag: M.W:100-200

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. 89976-56-7

A solution of 2,4-dimethoxybenzene-1-sulfonyl chloride (0.0799 g, 0.337 mmol) and 5-methylbenzo[d]isoxazol-3-amine I60 (0.050 g, 0.34 mmol) in pyridine (1 ml.) was irradiated in the microwave at 110 C for 2 hours. The resultant mixture was loaded onto silica gel and the product purified by column chromatography (12 g S1O2 cartridge, 0-45% EtOAc in petroleum benzine 40-60 C) [205] to yield the title compound (55.0 mg, 42% yield) as a white solid. NMR (400 MHz, CDCb) d 7.86 – 7.82 (m,1H), 7.72 (d, J = 8.81Hz, 1H), 7.37 – 7.28 (m, 2H), 6.49 (d, J = 2.26 Hz, 1H), 6.43 (dd, J = 2.29, 8.82 Hz, 1H), 3.96 (s, 3H), 3.80 (s, 3H), 2.47 (s, 3H). LCMS-A: rt 5.66 min, m/z 348.8 [M+H]+, 347.1 [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,89976-56-7,5-Methylbenzo[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

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, 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

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, 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. 239097-74-6

Synthesis of N-benzofdlisoxazol-5-yl-4-propyl-benzenesulfonamide, STX 919 (KRB01047) :; To a solution of 4n-propylbenzenesulphonyl chloride (171 mg, 0.783 mmol) in dichloromethane (4 mL) was added pyridine (150 uL, 1.86 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-1, 2-benzisoxazole (100 mg, 0.746 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 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 (170 mg, 72%), single spot at Rf 0.68 (1: 1 hexane: ethyl acetate). mp 130.0- 130. 6C, HPLC purity 99+% (tR 2.44 min in 10% water-acetonitrile).’H NMR (CDCI3) : No. 8.62 (1H, d, J=1.0 Hz), 7.60 (2H, d, J=8.4 Hz), 7.48 (2H, m), 7.19 (3H, m), 6.86 (1H, s, N-H), 2.58 (2H, t, J=7.5 Hz), 1.58 (2H, sextet, J=7.4 Hz), 0.88 (3H, t, J=7.4 Hz). LCMS: 315.14 (M-). FAB-MS (MH+, deHOsS) : calcd 317.0960, found 317.0962, 239097-74-6

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,239097-74-6,Benzo[d]isoxazol-5-amine,its application will become more common.

Reference£º
Patent; STERIX LIMITED; WO2005/42513; (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

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

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.

To a solution of 5-methyl-benzo[d]isoxazol-3-ylamine (4.6 g) in anhydrous DCM (50 mL) was slowly added a solution of (Boc)2O in anhydrous DCM (50 mL) and 50 mg of DMAP. After refluxing overnight, TLC showed complete reaction. LCMS/ELSD showed formation of the desired product (M+H: 349.2). The reaction was quenched with aqueous sodium carbonate (1 M, 50 mL) and stirred for 1 hr at room temperature. The organic layer was dried over anhydrous sodium sulfate. After rotary evaporation of most solvent, the concentrated solution was loaded onto a 50 g ISOLUTE silica cartridge and eluted with EtOAc/Hexane (from 1:10 to 1:2). Rotary evaporation of solvent provided a light yellow solid. Trituration with EtOAc/Hexane (1:9) provided a white solid (4.56 g). 1H-NMR (300 MHz, CDCl3) delta 7.47 (d, 1H), 7.40 (d, 1H), 7.37 (s, 1H), 2.48 (s, 3H), 1.41 (s, 18H). LC/MS (ESI): M+H+ 349.2.

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; Player, Mark R.; Lu, Tianbao; Hu, Huaping; Zhu, Xizhen; Teleha, Christopher; Kreutter, Kevin; US2007/225282; (2007); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics