Month: August 2020

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

3-Bromomethyl-benzo[d]isoxazole-5-sulfonyl chloride Chlorosulfonic acid (1.5 ml, 22 mmol) was slowly added to 3-Bromomethyl-benzo[d]isoxazole (1.0 g, 4.7 mmol) at RT under argon. The reaction was heated at 90 C. for 12 h and then left at RT for 6 h. The resulting viscous oil was quenched over ice, extracted with EtOAc, dried over MgSO4 and concentrated in vacuo to a brown oil (1.17 g, 80% yield).; 3-Bromomethyl-benzo[d]isoxazole-5-sulfonyl chloride Chlorosulfonic acid (1.5 ml, 22 mmol) was slowly added to 3-Bromomethyl-benzo[d]isoxazole (1.0 g, 4.7 mmol) at RT under argon. The reaction was heated at 90 C. for 12 h and then left at RT for 6 h. The resulting viscous oil was quenched over ice, extracted with EtOAc, dried over MgSO4 and concentrated in vacuo to a brown oil (1.17 g, 80% yield). After reaction of this material with the core the aliphatic bromine may be displaced by an appropriate nucleophile.

With the rapid development of chemical substances, we look forward to future research findings about 3-(Bromomethyl)benzo[d]isoxazole

Reference£º
Patent; Sequoia Pharmaceuticals; US2005/267074; (2005); 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 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.

As the paragraph descriping shows that 36216-80-5 is playing an increasingly important role.

Reference£º
Patent; Eli Lilly and Company; US4322429; (1982); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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

10% Palladium on carbon (1.5g) and triethylamine (7.5 g, 82.4 mmol) were added to a solution of ethyl 6-bromobenzisoxazole-3-carboxylate (20g, 0. 081mol) in ethanol (300ml) at 0 C under an atmosphere of nitrogen. The nitrogen atmosphere was removed by evacuation and replaced with hydrogen gas, and the reaction mixture was maintained for 1 hour. The hydrogen atmosphere was removed by evacuation and replaced with nitrogen gas, and the palladium removed by filtration through Celite. The filter cake was washed with ethanol (3 x 50 mL) and the filtrates were concentrated. The residue was dissolved in dichloromethane (200 mL) and the solution was washed with water (4 x 50 mL), dried (sodium sulfate) and evaporated to provide 13.0 g of the product as a yellow solid (96%). The ester was saponified using sodium hydroxide to provide the acid. The acid was coupled with the bicyclobase according to procedure A. Literature reference: Angell, R. M.; Baldwin, I. R.; Bamborough, P.; Deboeck, N. M.; Longstaff, T.; Swanson, S. W004010995A1 The following acid was prepared using this method: 1,2-Benzisoxazole-3-carboxylic acid.

As the rapid development of chemical substances, we look forward to future research findings about 651780-27-7

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/63767; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Benzo[d]isoxazol-5-amine, cas is 239097-74-6, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,239097-74-6

Synthesis of N-benzofdlisoxazol-5-vl-2, 5-dichloro-benzenesulfonamide, STX 920 (KRB01048):; To a solution of 2, 5-dichlorobenzenesulphonyl chloride (192 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 (174 mg, 68%), single spot at Rf 0.68 (1: 1 hexane: ethyl acetate). mp 172.9- 173. 6C, HPLC purity 99+% (tR 2.41 min in 10% water-acetonitrile).’H NMR (CDCI3) : 5 8.64 (1H, s), 7.89 (1H, d, J=2.2 Hz), 7.56-7. 28 (5H, m). LCMS: 341.07 (M-). FAB-MS (MH+, C13H8Cl2N2O3S) : calcd 342.9711, found 342.9710.

As the rapid development of chemical substances, we look forward to future research findings about 239097-74-6

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

Benzo[d]isoxazol-5-amine, cas is 239097-74-6, it is a common heterocyclic compound, the Benzisoxazole compound, its synthesis route is as follows.,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

As the rapid development of chemical substances, we look forward to future research findings about 239097-74-6

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

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) Mix tetrahydrofuran and triethylamine,Then add 5-chloro-3-phenyl-2,1 benzisoxazole,Palladium carbon catalyst mixing,Passing nitrogen,Replace the air 8 times,Then pass hydrogen to a pressure of 0.1 MPa.Magnetic stirring for 1h,Then filter,The obtained filter residue was vacuum dried at 50 C for 4 h.among them,Tetrahydrofuran,Triethylamine,5-chloro-3-phenyl-2,1 benzisoxazole,The mass ratio of the palladium carbon catalyst is 30:5:2:0.08,That is, 2-amino-5-chlorobenzophenone is obtained.

As the rapid development of chemical substances, we look forward to future research findings about 719-64-2

Reference£º
Patent; SHAANXI JUJIEHAN CHEMICAL CO LTD; Shanxi Jujiehan Chemical Co., Ltd.; LI CHANGYING; Li Changying; (4 pag.)CN107827763; (2018); 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).

As the rapid development of chemical substances, we look forward to future research findings about 36216-80-5

Reference£º
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.

The synthetic route of 36216-80-5 has been constantly updated, and we look forward to future research findings.

Reference£º
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

(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).

As the rapid development of chemical substances, we look forward to future research findings about 36216-80-5

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); 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

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]+

As the rapid development of chemical substances, we look forward to future research findings about 36216-80-5

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