Heterocyclic Building Blocks-Benzisoxazole

36216-80-5, Benzo[d]isoxazol-3-amine is a Benzisoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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

36216-80-5 Benzo[d]isoxazol-3-amine 2779749, aBenzisoxazole compound, is more and more widely used in various.

Reference£º
Patent; Hoechst-Roussel Pharmaceutical Incorporated; US5494908; (1996); A;,
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.

A mixture of benzo[d]isoxazol-3-amine and a sulfonyl chloride in pyridine (0.5 ml.) was stirred at room temperature for 64 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration and a portion of the crude material (50 mg or less) was purified by preparative mass-directed HPLC to give the desired product. See Table B for reaction components and amounts used.

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

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

719-64-2, 5-Chloro-3-phenylbenzo[c]isoxazole is a Benzisoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A, in a reaction vessel equipped with a stirrer, a reflux condenser, 5-chloro-3-phenyl-benzisoxazole 0.26 mol, the mass fraction of 30% 2-bromo-5-fluoronitrobenzene solution 390ml, nickel chloride powder 0.46 mol, control the stirring speed at 190 rpm, raise the solution temperature to 78 C, reflux reaction 120 min; B, adding 90% of 4-chlorophenethylamine solution with a mass fraction of 21% slowly add the ethylene glycol dimethyl ether solution with a mass fraction of 37% adding time to control at 110min, continue to reflux reaction 5h. C, add the mass fraction of 27% sodium bicarbonate solution 200ml, reduce the solution temperature to 16 C, molecular sieve bleaching, filtration, the filtrate was concentrated, again lowering the solution temperature to 5 C, the mass fraction of 70% triethylamine solution washing, calcium oxide dehydrating agent dehydration, to give crystals of 2-amino-5-chlorobenzophenone 55.59 g, yield 92%.

719-64-2 5-Chloro-3-phenylbenzo[c]isoxazole 347291, aBenzisoxazole compound, is more and more widely used in various.

Reference£º
Patent; Chengdu Qiesite Technology Co., Ltd.; Peng Fei; (9 pag.)CN106083621; (2016); A;,
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.

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).

36216-80-5 Benzo[d]isoxazol-3-amine 2779749, aBenzisoxazole compound, is more and more widely used in various.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/89753; (2005); A2;,
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.239097-74-6,Benzo[d]isoxazol-5-amine,as a common compound, the synthetic route is as follows.

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 paragraph descriping shows that 239097-74-6 is playing an increasingly important role.

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

36216-80-5, Benzo[d]isoxazol-3-amine is a Benzisoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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.

36216-80-5 Benzo[d]isoxazol-3-amine 2779749, aBenzisoxazole compound, is more and more widely used in various.

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

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.

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.

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

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/153752; (2008); A2;,
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.719-64-2,5-Chloro-3-phenylbenzo[c]isoxazole,as a common compound, the synthetic route is as follows.

1) Weigh 180 g of raw material 5-chloro-3-phenyl-2,1-benzisoxazole into 1.5 L of anhydrous methanol and 1.5 L of acetonitrile,After stirring and dissolving, add 10g Pd/C catalyst with Pd content of 3%, stir and mix to form material I,The flow rate of the slurry pump was adjusted so that the flow rate of the material I was 40.0 g/min and entered the preheating module of the microreactor. 2) Adjust the flow rate of the H2 gas flowmeter to 350ml/min, and directly enter the reaction module group and material I to undergo catalytic hydrogenation reaction without preheating.As shown in Figure 2, the molar ratio of 5-chloro-3-phenyl-2,1-benzisoxazole to hydrogen is 1:1.2, the reaction temperature is 80C, the residence time of the reaction is 35s, and the reaction pressure is 1.0Mpa; then enter the cooling module, cooling module temperature is 30 C,Collect the reaction solution from the outlet of the cooling module, recover the catalyst by filtration, and recover the solvent by distillation under reduced pressure.The residue was recrystallized from 80% ethanol solution to obtain the target product 2-amino-5-chlorobenzophenone, 168.96g, yield 92.79%, purity 99.68%.

As the paragraph descriping shows that 719-64-2 is playing an increasingly important role.

Reference£º
Patent; Heilongjiang Xinchuang Bio-technology Development Co., Ltd.; Ren Jiqiu; Yang Kun; Li Haitao; (10 pag.)CN107935872; (2018); A;,
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.

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+).

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

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

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.

Example 148: N-(benzo[d]isoxazol-3-yl)-2,4-dimethoxybenzenesulfonamide 148 A solution of 2,4-dimethoxybenzenesulfonyl chloride (0.18 g, 0.75 mmol) and benzo[d]isoxazol-3-amine (0.10 g, 0.75 mmol) in pyridine (1 ml.) was irradiated in the microwave at 1 10 C for 2 hours. The resultant mixture was loaded onto silica gel and the product purified twice by column chromatography (4 g Si02 cartridge, 0-45% EtOAc in petroleum benzine 40-60 C then 4g Si02 cartridge, 0-35% EtOAc in petroleum benzine 40-60 C) to yield two batches (78 mg and 5 mg) of [183] the title compound (total mass 83 mg, 33 % yield) as white solids. 1H NMR (400 MHz, CDCI3) d 8.1 1 (d, J = 8.05 Hz, 1H), 7.79 (s, 1H), 7.70 (d, J = 8.81Hz, 1H), 7.57 – 7.50 (m, 1H), 7.47 – 7.40 (m, 1H), 7.37 – 7.29 (m, 1H), 6.50 (d, J = 2.27 Hz, 1H), 6.42 (dd, J = 2.25, 8.81Hz, 1H), 3.98 (s, 3H), 3.81 (s, 3H). LCMS-B: rt 3.20 min, m/z = 356.8 [M+Na]+, 334.8 [M+H]+.

36216-80-5 Benzo[d]isoxazol-3-amine 2779749, aBenzisoxazole compound, is more and more widely used in various.

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