Heterocyclic Building Blocks-Benzisoxazole

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.,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

As a common heterocyclic compound, it belongs to Benzisoxazole compound, name is 3-(Bromomethyl)benzo[d]isoxazole, and cas is 37924-85-9, its synthesis route is as follows.,37924-85-9

(b) A solution containing 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)-imidazole (6.7 g, 0.025 mole), and 3-bromomethyl-1,2-benzisoxazole (5.3 g, 0.025 mole) in anhydrous acetonitrile (30 mL) is stirred at reflux for 72 hours. The reaction mixture is cooled and mixed with a solution of sodium methoxide (3 g, 0.055 mole) in methanol (30 mL). The resulting solution is stirred at reflux for 26 hours. The solvents are evaporated and the residue is taken up in 1N hydrochloric acid (30 mL). This solution is allowed to stand at ambient temperature for 3 hours and is then made basic (pH 9) by addition of 50% aqueous sodium hydroxide solution. The mixture is extracted with methylene chloride (2*25 mL) and the combined extracts are washed with water (2*20 mL), dried over anhydrous sodium sulfate, filtered, and the solvent is evaporated to give crude 3-[(5-(3-hydroxypropyl)-1H-imidazol-1-yl)methyl]-1,2-benzisoxazole which is purified by trituration with acetone (15 mL), m.p. 129-131 C.

With the complex challenges of chemical substances, we look forward to future research findings about 37924-85-9,belong Benzisoxazole compound

Reference£º
Patent; Ciba-Geigy Corporation; US4859691; (1989); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

As a common heterocyclic compound, it belong Benzisoxazole compound,3-(Bromomethyl)benzo[d]isoxazole,37924-85-9,Molecular formula: C8H6BrNO,mainly used in chemical industry, its synthesis route is as follows.,37924-85-9

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.

With the synthetic route has been constantly updated, we look forward to future research findings about 3-(Bromomethyl)benzo[d]isoxazole,belong Benzisoxazole compound

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

As a common heterocyclic compound, it belong Benzisoxazole compound,Benzo[d]isoxazol-3-amine,36216-80-5,Molecular formula: C7H6N2O,mainly used in chemical industry, its synthesis route is as follows.,36216-80-5

(Synthesis of X-4) In a three-neck flask, after filling the inside of flask with nitrogen gas, 6.5 g of 10% Pd-C (produced by Wako Pure Chemical Industries, Ltd.) was added, and 2,000 mL of ethanol and the entire amount of the crude product of Compound (X-3) obtained above were further added. The resulting mixture was heated/refluxed, and 55 mL (3 molar equivalents) of formic acid was slowly added dropwise thereto, followed by stirring at this temperature for 5 hours. The resulting reaction mixture was cooled to an inner temperature of 25C and then subjected to Celite filtration and to the mother solution separated by filtration, 105 g of 1,5-naphthalenedisulfonic acid was added. After raising the inner temperature to 70C, the mixture was stirred for 30 minutes and then gradually cooled to room temperature, and the crystal was separated by filtration to obtain 100 g of Compound (X-4). The yield was 72% based on Compound (X-1) as the starting material. The obtained crystal was pale brown. 1H NMR (deuterated DMSO): delta6.95-6.98 (1H), delta7.02-7.04 (1H), delta7.40-7.51 (3H), delta7.90-7.95 (1H), delta8.75 (1H), delta8.85-8.88 (2H), delta9.03 (2H), delta10.89 (1H).

With the synthetic route has been constantly updated, we look forward to future research findings about Benzo[d]isoxazol-3-amine,belong Benzisoxazole compound

Reference£º
Patent; FUJIFILM Corporation; EP2460799; (2012); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO70,mainly used in chemical industry, its synthesis route is as follows.,36216-80-5

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.

With the complex challenges of chemical substances, we look forward to future research findings about Benzo[d]isoxazol-3-amine,belong Benzisoxazole compound

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

As a common heterocyclic compound, it belongs to Benzisoxazole compound, name is 3-(Bromomethyl)benzo[d]isoxazole, and cas is 37924-85-9, its synthesis route is as follows.,37924-85-9

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.

With the complex challenges of chemical substances, we look forward to future research findings about 37924-85-9,belong Benzisoxazole compound

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

As a common heterocyclic compound, it belong Benzisoxazole compound,Benzo[d]isoxazol-3-amine,36216-80-5,Molecular formula: C7H6N2O,mainly used in chemical industry, its synthesis route is as follows.,36216-80-5

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

With the synthetic route has been constantly updated, we look forward to future research findings about Benzo[d]isoxazol-3-amine,belong Benzisoxazole compound

Reference£º
Patent; Hoechst-Roussel Pharmaceutical Incorporated; US5494908; (1996); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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

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).

With the synthetic route has been constantly updated, we look forward to future research findings about Benzo[d]isoxazol-3-amine,belong Benzisoxazole compound

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