Category: Benzisoxazole

Benzo[d]isoxazol-3-amine, cas is 36216-80-5, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,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+).

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Patent; Pfizer Inc.; US2010/113465; (2010); A1;,
Benzisoxazole – Wikipedia
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Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, cas is 651780-27-7, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,651780-27-7

Step 3 6-(4-Hvdroxy-2-methyl-phenyl’)-benzordlisoxazole-3-carboxylic acid ethyl esterA solution of 3-methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenol (0.624 g, 2.67 mmol) and 6-bromo-benzo[d]isoxazole-3-carboxylic acid ethyl ester (0.360 g, 1.33 mmol) in 1,4-dioxane (20 mL) is added to a flask. The flask is evacuated and re-filled with N2 3 times. To this solution, Pd2(dba)3 (0.010 g), tricyclohexyl phosphine (10 mg), and aqueous K3PO4 (1.5 mL, 1.30 M) are added. The resulting mixture is heated to 50 C for 2 hours under N2. The reaction mixture is cooled to room temperature and filtered through a pad of diatomaceous earth. The filtrate is concentrated under reduced pressure. The residue is purified via silica gel chromatography eluting with 25% ethyl acetate in hexanes to give the title compound (0.366 g, 93%). ES/MS m/e 298.0 (M+l); 296.0 (M-I).

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Patent; ELI LILLY AND COMPANY; WO2007/92751; (2007); A2;,
Benzisoxazole – Wikipedia
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5-Methylbenzo[d]isoxazol-3-amine, cas is 89976-56-7, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,89976-56-7

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%).

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Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Benzisoxazole – Wikipedia
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Benzo[d]isoxazol-3-amine, cas is 36216-80-5, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,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.

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Patent; Eli Lilly and Company; US4336264; (1982); A;,
Benzisoxazole – Wikipedia
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3-(Bromomethyl)benzo[d]isoxazole, cas is 37924-85-9, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,37924-85-9

BIOS-Na (Compound III) was prepared in accordance with the method described in Example 1 of U.S. Pat. No. 4,172,896. A solution of sodium sulfite (24.3 grams) in water (390 ml) was added to a solution of 3-bromomethyl-1,2-benzisoxazole (24 grams, Compound II) in methanol (390 ml), stirred with heating to 50 C. for 4 hours. After completion of the reaction, the solution was concentrated under reduced pressure. The resulting crystalline residue was heated to about 50-60 C. in methanol (750 ml) and the solution filtered. The clear filtrate was concentrated under reduced pressure and the resulting crystalline residue was washed with diethyl ether to give crystalline sodium 1,2-benzisoxazole-3-methanesulfonate (18 grams, BIOS-Na, Compound III). Thc thus-produced BIOS-Na was analyzed using X-Ray powder diffraction (results depicted in FIG. 1), differential scanning calorimetry (results depicted in FIG. 2) and thermal gravimetry (results depicted in FIG. 3). The water content of the thus-produced BIOS-Na was 7% as measured by Karl-Fischer titration, indicating that the crystals were of BIOS-Na monohydrate.

37924-85-9 is used more and more widely, we look forward to future research findings about 3-(Bromomethyl)benzo[d]isoxazole

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Patent; Naddaka, Vladimir; Adin, Itai; Klopfer, Eyal; Arad, Oded; Kaspi, Joseph; US2006/9644; (2006); A1;,
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5-Chloro-3-phenylbenzo[c]isoxazole, cas is 719-64-2, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,719-64-2

(3) According to a mass ratio of 30:2:0.08:1.7, methanol, 5-chloro-3-phenyl-2,1benzisoxazole, palladium-carbon catalyst, and ammonium formate were mixed and heated to reflux at 50C for 2 hours. After allowing to cool to room temperature, the mixture was filtered, and the resulting residue was vacuum dried at 50C for 4 hours to obtain 2-amino-5-chlorobenzophenone.

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Patent; Shanxi Jujiehan Chemical Co., Ltd.; Li Changying; (5 pag.)CN107698453; (2018); A;,
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A common heterocyclic compound, the Benzisoxazole compound, name is Benzo[d]isoxazol-3-amine,cas is 36216-80-5, mainly used in chemical industry, its synthesis route is as follows.,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]+

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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

A common heterocyclic compound, the Benzisoxazole compound, name is Benzo[d]isoxazol-3-amine,cas is 36216-80-5, mainly used in chemical industry, its synthesis route is as follows.,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).

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36216-80-5,Benzo[d]isoxazol-3-amine,as a common compound, the synthetic route is as follows.,36216-80-5

EXAMPLE 12 3-[(4-pyridinyl)amino]-1,2-benzisoxazole A mixture of 3-amino-1,2-benzisoxazole (9.94 g, 74.18 mmole, prepared according to a method described in G. M. Shutske and K. J. Kapples, J. Heterocyclic Chem., 26, 1293 (1989)), 4-chloropyridine hydrochloride (22.27 g, 197 mmole) and 1-methyl-2-pyrolidinone was stirred vigorously at 130 C. for three hours. The reaction mixture was cooled, diluted with NaHCO3, and extracted with EtOAc, after which the organics were washed with water, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (florisil, EtOAc), and then triturated with diethyl ether to yield 4.04 g (26%) of a fine brown solid. A 2.0 g portion was dissolved in boiling methanol and treated with charcoal (Darco) after which the product crystallized to yield 1.38 g of pale yellow crystals, mp 203 C. (dec.). ANALYSIS: Calculated for C12 H9 N3 O: 68.24% C; 4.29% H; 19.89% N; Found: 68.14% C; 4.12% H; 20.06% N.

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Patent; Hoechst-Roussel Pharmaceuticals Incorporated; US5328920; (1994); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, the Benzisoxazole compound, name is Benzo[d]isoxazol-3-amine,cas is 36216-80-5, mainly used in chemical industry, its synthesis route is as follows.,36216-80-5

Example 24; N-1,2-Benzisoxazol-3-yl-1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxamide; [Show Image] To a solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylic acid (289 mg, 1.00 mmol) and N,N-dimethylformamide (0.010 ml) in tetrahydrofuran (5 ml) was added in water-bath, oxalyl chloride (0.174 ml, 2.00 mmol), and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was added to a solution of 1,2-benzisoxazol-3-amine (134 mg, 1.00 mmol) in pyridine (0.404 ml, 5.00 mmol) under ice-cooling, followed by stirring at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue 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. The residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1) to give the desired product as a solid. The resulting solid was recrystallized from a mixed solvent of hexane and ethyl acetate to give 60.3 mg (14.9%) of the desired product. 1H-NMR (CDCl3) delta; 2.05 – 2.22 (4H, m), 2.88 (1H, br s), 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).

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