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 4: (R)-l-(Benzo[rf]isoxazol-3-yIcarbamoylmethyl)-3-(l-phenyl- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane bromide To a mixture of benzo[Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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.

To a stirred solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine- 4-carboxylic acid (289 mg, 1.00 mmol) and DMF (0.010 mL) in THF (5.0 mL) was added oxalyl chloride (0.174 mL, 2.00 mmol) dropwise at 0 C. After stirring at room temperature for 1 h, the solvent was concentrated in vacuo. To the residue were added THF (5.0 mL), benzo[d]isoxazol-3-amine (134 mg, 1.00 mmol), and pyridine (0.404 mL, 5.00 mmol) at 0 C. The mixture was stirred at room temperature for 1.0 h, and the solvent was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc), and recrystallized from EtOAc- hexane to give 65a (60.3 mg, 15%) as colorless crystals, mp 204- 205 C. 1H NMR (300 MHz, CDCl3) d: 2.05-2.22 (4H, m), 2.88 (1H, bs), 3.36-3.45 (2H, m), 4.11-4.18 (2H, m), 7.32-7.63 (6H, m), 8.19-8.27 (3H, m), 9.46 (1H, br s). Analytical HPLC showed 97.4% purity., 36216-80-5

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; Kono, Mitsunori; Matsumoto, Takahiro; Kawamura, Toru; Nishimura, Atsushi; Kiyota, Yoshihiro; Oki, Hideyuki; Miyazaki, Junichi; Igaki, Shigeru; Behnke, Craig A.; Shimojo, Masato; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 28 – 41;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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.

Synthesis of phenyl 1,2-benzisoxazol-3-ylcarbamate; A solution of 1,2-benzisoxazol-3-amine (1.00 g; CAS No.36216-80-5) and triethylamine (1.09 mL) in acetonitrile (5 mL) was added dropwise to at 0 C. solution of phenyl chloroformate (0.989 mL) in THF (20 mL). The reaction was stirred at 0 C. for 1 h and then allowed to warm to room temp overnight. The reaction was diluted with ethyl acetate and washed with 1N HCl 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.; US2010/113465; (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

Under nitrogen benzo [d] isoxazol-3-amine (3.6g, 26.8mmol) was dissolved in chlorosulfonic acid (15.0mL), heated to 60 stirred overnight.Cooled to room temperature, ice water (20 mL), suction filtered, the filter cake was dried at 60 deg.] C under vacuum to give a white solid (5.0g, 87%)., 36216-80-5

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; Guangdong East sunshine Pharmaceutical Co; Zuo, Yinglin; Zheng, Jinfu; Wen, Liang; Zhang, Min; Wu, Shoutao; Yuan, Xiaofeng; Lin, Runfeng; Wang, Xiaojun; Zhang, Yingjun; (27 pag.)CN104530046; (2016); B;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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.

General procedure: To a stirred solution of pyridin-2-amine (1.0 g, 10.6 mmol) and pyridine (1.01 mL, 12.7 mmol) in THF (35 mL) was added 2,2,2- trichloroethyl chloroformate (1.76 mL, 12.7 mmol) dropwise at 0 C. The mixture was stirred at 0 C for 1.5 h, poured into water, and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was triturated with Et2O-hexane to give 36 (1.76 g, 62%) as a colorless powder.

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
Article; Kono, Mitsunori; Matsumoto, Takahiro; Kawamura, Toru; Nishimura, Atsushi; Kiyota, Yoshihiro; Oki, Hideyuki; Miyazaki, Junichi; Igaki, Shigeru; Behnke, Craig A.; Shimojo, Masato; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 28 – 41;,
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

Synthesis of phenyl 1,2-benzisoxazol-3-ylcarbamate; A solution of 1,2-benzisoxazol-3-amine (1.00 g; CAS No.36216-80-5) and triethylamine (1.09 mL) in acetonitrile (5 mL) was added dropwise to at 0 C. solution of phenyl chloroformate (0.989 mL) in THF (20 mL). The reaction was stirred at 0 C. for 1 h and then allowed to warm to room temp overnight. The reaction was diluted with ethyl acetate and washed with 1N HCl 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+)., 36216-80-5

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; Pfizer Inc.; US2010/113465; (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

Phenyl 1 ,2-benzisoxazol-3-ylcarbamateA 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 RT 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 RT, and filtered to give 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.; LONG, Scott Allen; MEYERS, Marvin Jay; PELC, Matthew James; SCHWEITZER, Barbara Ann; THORARENSEN, Atli; WANG, Lijuan Jane; WO2010/58318; (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

a) N-Benzo[d]isoxazol-3-yl-2-chloro-acetamide To a mixture of benzo[d]isoxazol-3-ylamine (1 g) and cesium carbonate (2.42 g) in dry DMF (20 mL), stirred at rt, was added bromoacetyl chloride (0.62 mL) by dropwise addition. After stirring the mixture for 8 hours, the reaction was poured into water (100 mL) and the products extracted into ether (2*200 mL). The combined extracts were dried over magnesium sulfate and concentrated to dryness. The crude product was purified on silica gel using ether/isohexane (4/6) to afford the sub-titled compound as a colourless solid (0.5 g). m/e 210 [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; Bull, Richard James; Skidmore, Elizabeth Anne; Ford, Rhonan Lee; Mather, Andrew Nigel; Mete, Antonio; US2011/172237; (2011); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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.

A mixture of intermediate 3 (0.0025 mol) and triethylamine (0.0025 mol) in CHzClz (10 ml) was stirred at RT. 2-methylpropanoyl chloride (0.0025 mol) was added dropwise and the reaction mixture stirred overnight at RT. The reaction mixture was washed 2 times with H20. The organic layer was separated, dried (MgS04), filtered off and the solvent was evaporated dry. The residue was further purified by column chromatography over silicagel (eluent: CH2Cl2) yielding 0.235 g of compound 8 and a fraction which was further purified using reversed phase HPLC chromatography on a Xterra MS C18 column (3. 5, um, 4.6 x 100 mm) with a flow rate of 1.6 m ./min (Elution conditions: three mobile phases (mobile phase A 95% 25mM ammoniumacetate + 5% acetonitrile; mobile phase B: acetonitrile ; mobile phase C: methanol) were employed to run a gradient condition from 100 % A to 50% B and 50% C in 6.5 min. , to 100 % B in 1 min, 100% B for 1 min. and re-equilibrate with 100 % A for 1.5 min.) yielding 0.010 g of compound 7 (Melting Point 130C).

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.; WO2005/89753; (2005); 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 4: (R)-l-(Benzo[rf]isoxazol-3-yIcarbamoylmethyl)-3-(l-phenyl- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane bromide To a mixture of benzo[Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics