Day: May 18, 2021

36216-80-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Benzo[d]isoxazol-3-amine, cas is 36216-80-5,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of triethylamine (0. 0025 mol) in CH2Cl2 (5 ml) benzoylchloride (0.0025 mol) was added. The mixture stirred at RT and intermediate 3 (0.0025 mol) in CH2C12 (5 ml) added dropwise. The reaction mixture was stirred overnight at RT. The mixture was washed 2 times with H20. The organic layer was separated, dried (MgS04), filtered off and the solvent was evaporated. The residue was purified by column chromatography over silicagel (eluent CH2Cl2) yielding O. OlOg compound 9 (yield of 2%, Melting Point 133C) and a fraction which was further purified by column chromatography over silicagel (eluent hexane/CH2Cl2) yielding 0.225 g of compound 10 (yield of 38%, Melting Point 97C-100C), and 0.100 g of compound 11 (yield of 17%, Melting Point 154C-160C).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Benzo[d]isoxazol-3-amine, 36216-80-5

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/89753; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

As a common heterocyclic compound, it belongs to Benzisoxazole compound, name is Benzo[d]isoxazol-3-amine, and cas is 36216-80-5, its synthesis route is as follows.

A 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 room temp 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 room temp, and filtered to give the final product as a tan solid (1.22 g, 64%). m/z 255 (MH+).

36216-80-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,36216-80-5 ,Benzo[d]isoxazol-3-amine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; PFIZER INC.; WO2009/127948; (2009); A1;; ; Patent; PFIZER INC.; WO2009/127949; (2009); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Name is Benzo[d]isoxazol-3-amine, as a common heterocyclic compound, it belongs to Benzisoxazole compound, and cas is 36216-80-5, its synthesis route is as follows.

(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).

36216-80-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,36216-80-5 ,Benzo[d]isoxazol-3-amine, other downstream synthetic routes, hurry up and to see

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

651780-27-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, cas is 651780-27-7,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

Diethyl malonate (12.6 g, 79 mmol) was added to a suspension of sodium hydride (3.16 g, 132 mmol) in dimethylsulfoxide (60 ml) over 30 min. The temperature of the reaction rose to 60 C and the mixture clarified. 1,4-Dibromo-2-nitrobenzene (10 g, 36.0 mmol) was added and the solution was maintained for 2 h at 100 C. The reaction mixture was allowed to cool to rt and was poured into ice (300g-400g). The precipitated solids were isolated by filtration and dried to provide 11.0 g of the product (89%). The ester (11.0 g, 32.0 mmol) was diluted with a 2 N solution of sodium hydroxide (32 mL, 63 mmol) and the reaction mixture was maintained at room temperature for 16 h. The aqueous layer was extracted with dichloromethane (20 mL) and was acidified. The precipitated solids were isolated by filtration and dried to provide 7.00 g of the acid (89%). Sulfuric acid (1 mL) was added to a solution of the acid (7.00 g, 27.0 mmol) in ethanol (60 ml). The reaction mixture was warmed to reflux, maintained for 2 h, and was concentrated under reduce pressure. The residue was partitioned between ethyl acetate (250 mL) and saturated sodium carbonate (50 mL) and the organic layer was washed with saturated sodium carbonate (50 mL) and brine (50 mL). The organic layer was dried (sodium sulfate) and concentrated to provide 8.00 g (98%) of the ester as a liquid. Under N2 atmosphere, sodium ethylate was formed with sodium (33.5 g, 1.46 mol) in ethanol (1.0 L). Isoamylnitrite (225 mL) was added to a solution of the ester (420 g, 1.46 mol) in ethanol (3 L) in a 10 L three-necked round bottom flask and the mixture was warmed to 60 C. A solution of sodium ethoxide, prepared from sodium metal (33.5 g, 1.46 mmol) in ethanol (1 L) was added dropwise and the reaction mixture was maintained for 2 h. The reaction mixture was allowed to cool to rt and was neutralized with 2 N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (4 x 2L) and the combined organic layers were washed with water (2 x 1 L) and brine (2 x 1 L) and dried (sodium sulfate). The residue was purified by chromatography (1/1 to 0/1 hexane/ethyl acetate) to provide 110 g of the product ( 28%). 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 1,4-diazabicyclo[3.2.2]nonane according to procedure A.

The chemical industry reduces the impact on the environment during synthesis,651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/111038; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

719-64-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chloro-3-phenylbenzo[c]isoxazole, cas is 719-64-2,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

The preparation method is as follows: 5-chloro-3-phenyl 2,1-benzisoxazole (commercially available) (0.3 mmol, 68.7 mg), phenylacetaldehyde (0.6 mmol, 72.0 mg), copper powder (0.06) Methanol, 3.8 mg) and silver triflate (0.03 mmol, 8.0 mg) were added to a 25 ml Schlenk tube, and the reaction tube was replaced with oxygen three times under reduced pressure.Hexafluoroisopropanol (2 ml) was added and stirred at 110 C for 30 hours.After completion of the reaction, a column chromatography of silica gel of 100-200 mesh was added, and the solvent was evaporated under reduced pressure. The crude product was subjected to silica gel column chromatography, eluting with petroleum ether and ethyl acetate ( petroleum ether: ethyl acetate = 20:1) The liquid was eluted, and the elution was carried out by TLC elution. The eluate containing the desired product was collected, and the desired product eluent was combined and evaporated to give the quinoline compound of the formula i above, yield 69%. This material is a red solid.

The chemical industry reduces the impact on the environment during synthesis,719-64-2,5-Chloro-3-phenylbenzo[c]isoxazole,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Jiangnan University; Zou Lianghua; Zhu Hao; Zhu Shuai; Li Pinggui; Yan Cheng; (12 pag.)CN110204486; (2019); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Name is Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, as a common heterocyclic compound, it belongs to Benzisoxazole compound, and cas is 651780-27-7, its synthesis route is as follows.

10% Palladium on carbon (1.5 g) and triethylamine (7.5 g, 82.4 mmol) were added to a solution of ethyl 6-bromobenzisoxazole-3-carboxylate (20 g, 0.081 mol) 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¡Á50 mL) and the filtrates were concentrated. The residue was dissolved in dichloromethane (200 mL) and the solution was washed with water (4¡Á50 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.

651780-27-7, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,651780-27-7 ,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; Xie, Wenge; Herbert, Brian; Ma, Jianguo; Nguyen, Truc Minh; Schumacher, Richard; Gauss, Carla Maria; Tehim, Ashok; US2005/250808; (2005); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Benzo[d]isoxazol-3-amine, cas is 36216-80-5,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of benzo[d]isoxazol-3-amine (1 eq.) and quinuclidin-3-one (1.1 eq.) in toluene (7 mL/mmol benzo[d]isoxazol-3-amine) at 25 C was added portion-wise titanium(IV) isopropoxide (9 eq.). The resulting solution was stirred at 100 C for 12 hours. On completion, the mixture was cooled to 0 C, and ethanol (1 mL/mmol benzo[d]isoxazol-3-amine) was added via syringe, followed by sodium borohydride (3.7 eq.) in portions. The reaction was stirred at 25 C for 3 hours, then quenched with saturated aqueous potassium carbonate solution, resulting in the formation of a solid. The mixture was filtered, and the filtrate was extracted with dichloromethane (5 chi 50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The filter cake from the original filtration was slurried with methanol, and the mixture was filtered. The filtrate was directly evaporated to dryness. The combined residue from both batches was dissolved in 4N hydrochloric acid (20 mL) and stirred at room temperature for 4 hours. The mixture was made basic by addition of saturated potassium carbonate solution and extracted with dichloromethane (5 x 50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to give the racemic aminobenzoisoxazole product. [00408] Chiral Separation: A solution of racemic aminobenzoisoxazole product in 3-5 mL of methanol was separated by cSFC (Waters SFC Prep 80, Column temperature: 25 C, back pressure: 100 bar, and wavelength: 220 nm). Each set of collected fractions was concentrated at room temperature. The residue was dissolved in 0.2 M hydrochloric acid and lyophilized to give each enantiomer of the aminobenzoisoxazole product; Following general procedure Bl, rac-1 was prepared from benzo[d]isoxazol-3 -amine (0.40 g, 3.0 mmol). The product was purified by prep-HPLC [Instrument: GX-A; Column: Phenomenex Gemini C18 150×25 mm, particle size: 10 mupiiota; Mobile phase: 44-74% acetonitrile in H20 (add 0.5% NH3 H20, v/v)] to give rac-1 (70 mg, 9% yield) as a yellow solid. LCMS (B): tPv=1.179 min., (ES+) m/z (M+H)+ = 244.2.

The chemical industry reduces the impact on the environment during synthesis,36216-80-5,Benzo[d]isoxazol-3-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (127 pag.)WO2016/201096; (2016); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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

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.

36216-80-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,36216-80-5 ,Benzo[d]isoxazol-3-amine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; TARGACEPT, INC.; MAZUROV, Anatoly A.; MIAO, Lan; SHOWALTER, Todd; WO2013/28587; (2013); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

239097-74-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Benzo[d]isoxazol-5-amine, cas is 239097-74-6,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

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

The chemical industry reduces the impact on the environment during synthesis,239097-74-6,Benzo[d]isoxazol-5-amine,I believe this compound will play a more active role in future production and life.

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

37924-85-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3-(Bromomethyl)benzo[d]isoxazole, cas is 37924-85-9,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

Step 1: To a -78 C solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[bl[1,4ldiazepin- 3-yl)-carbamic acid tert-butyl ester (807 mg, 2.91 mmol) in THF (19.4 mL) was added lithium bis(trimethylsilyl)amide (3.2 mL, 1.0 M solution in THF, 3.2 mmol), dropwise. The mixture was stirred at -78 C for 15 mm, then a mixture of Nal (523 mg, 3.49 mmol) and 3- (bromomethyl)benzo[dlisoxazole (740 mg, 3.49 mmol) in THF (9.7 mL) was added dropwise over 10 mm. The mixture was stirred at -78 C for 50 mm., warmed to RT and stirred for 4.5 h. The mixture was diluted with 1 N citric acid and extracted with EtOAc. The combined extractswere washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide a -4:1 mixture of (S)-tert-butyl 1-(benzo[dlisoxazol-3-ylmethyl)-2- oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1 ,4jdiazepin-3-ylcarbamate and (S)-tert-butyl 1- (benzo [djisoxazol-3 -ylmethyl)-4-oxo-2,3 ,4,5 -tetrahydro- 1 H-benzo [bI [1,41 diazepin-3-ylcarbamate (742 mg, 63 %) as a yellow foam. LC-MS mlz 431 [M+Naj.Step 1: To a 0C solution of -4:1 mixture of tert-butyl (S)-1-((S)-1-(benzo[djisoxazol-3- ylmethyl)-2-oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1,41 diazepin-3 -ylamino)- 1 -oxopropan-2- yl(methyl)carbamate and tert-butyl (S)-i -((S)-i -(benzo[dlisoxazol-3-ylmethyl)-4-oxo-2,3 ,4,5- tetrahydro- 1 H-benzo [bI [1 ,4ldiazepin-3-ylamino)- 1 -oxopropan-2-yl(methyl)carbamate (209.4 mg, 424 tmol) in CH2C12 (4.24 mL) was added pyridine (343 tL, 4.24 mmol), followed by methyl 4-(chlorocarbonyl)benzoate (92.7 mg, 467 tmol). After 1 h at 0 C the mixture was diluted with H20 and extracted with CH2C12. The combined extracts were washed with 1 N aq. citric acid, sat. aq. NaHCO3, and brine, dried over Na2504, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide methyl 4-((S)-5-(benzo[djisoxazol-3 -ylmethyl)-3 -((S)-2-(tert-butoxycarbonyl(methyl)amino) propanamido)-4-oxo-2,3 ,4,5 -tetrahydro- 1 Hbenzo[b l[1,4ldiazepine-1-carbonyl)benzoate (194 mg, 70 %) as a white solid. LC-MS mlz 678 [M+Naj .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-(Bromomethyl)benzo[d]isoxazole, 37924-85-9

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Shaoqing; DONNELL, Andrew F.; KESTER, Robert Francis; LE, Kang; LOU, Yan; MICHOUD, Christophe; REMISZEWSKI, Stacy; RUPERT, Kenneth C.; WEISEL, Martin; WO2015/71393; (2015); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics