Some tips on 274910-19-9

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various fields.

274910-19-9, (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,274910-19-9

N5-Cyclobutyl-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-d icarboxamide (50 mg, 0.201mmol), (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol (50.0 mg, 0.301 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.166 mL, 0.632 mmol) were combined in toluene (1.5 mL)and the reaction mixture heated in a 5 mL microwave vial on a Biotage Initiator microwave at 120C for 30 mm. The reaction mixture was poured onto water (20 mL), and extracted with ethylacetate (3 x 10 mL). The combined organic portions were evaporated in vacuo to yield the crude product as a brown oil. The product was loaded in dichloromethane onto a 25 g SNAP silica cartridge and purified via Biotage 5P4 flash chromatography, eluting from 50 – 100 % ethyl acetate/cyclohexane. The relevant fractions were combined and evaporated in vacuo – yielding 76mg of product. The sample was dissolved in MeOH/DMSO (1 mL, 1:1) and purified by MDAP (Formic). The solvent was evaporated in vacuoto give the required product – N5-cyclobutyl-1-((2,3- dihyd robenzo[b] [1,4]d ioxin-5-yl)methyl)-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-dicarboxamide(40 mg, 0.096 mmol, 47.7 % yield).LCMS (2 mm Formic): Rt = 0.95 mi [MH] = 398.1.

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Downstream synthetic route of 274910-19-9

As the paragraph descriping shows that 274910-19-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.274910-19-9,(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,as a common compound, the synthetic route is as follows.

A solution of 2,3-dihydro-1,4-benzodioxin-5-ylmethanol (Intermediate A1) (commercially available from Aldrich) (3 g, 18.1 mmol) in THF (100 mL) was treated with manganese(IV) oxide, activated (commercially available from Aldrich): MnO2 (10 g, 115 mmol) at rt. The mixture was heated to 35 C. for 2 h and 60 C. for 4 h followed by 18 h at room temperature (rt). The mixture was filtered through celite and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 20% EtOAc:hexanes to give 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) 2.6 g (88%). A mixture of 4-iodo-1-tritylimidazole (commercially available) (8.64 g, 19.8 mmol) in dichloromethane (100 mL) at -10 C. was treated with ethyl magnesium bromide (6.3 mL, 19 mmol, 3M in THF) and allowed to react for 45 m. A solution of 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) (2.6 g, 15.9 mmol) in dichloromethane was added via syringe at -10 C. and stirred for 45 m. The mixture was quenched with water (50 mL) and a sat. solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by chromatography on silica gel with 3 to 5% NH3-MeOH:CH2Cl2 to give (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) as a solid, 2.9 g (40%). A solution of (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) (1 g, 2.11 mmol) in dichloromethane (30 mL) was reacted with TFA:trifluoroacetic acid (5.3 mL, 68 mmol)) and triethylsilane (TES) (2.8 mL, 17 mmol) at rt for 24 h. The mixture was evaporated under reduced pressure and quenched with solid NaHCO3. This material was subjected to an aqueous work-up and the residue was purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to yield 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole (Intermediate A4) 330 mg (72%). A mixture of 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole (Intermediate A4) (260 mg, 1.2 mmol) in THF (10 mL) and water (10 mL) was treated with NaHCO3 (1 g, 12 mmol) and phenylchlorothionoformate (0.42 mL, 3.13 mmol) for 3 h at rt. The mixture was diluted with diethyl ether (35 mL) and water (10 mL). The aqueous layer was removed and extracted with ether (2¡Á10 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under vacuum. The residue was treated with triethylamine (1 mL) in methanol (9 mL) at rt for 16 h. The solvent was removed and the product was isolated and purified either by tituration with CH2Cl2:hexane or by chromatography on SiO2 with EtOAc or 3% MeOH:CH2Cl2. This gave 4-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound-1) 150 mg (50%). 1H NMR (300 MHz, DMSO-d6 w/TMS): delta 11.9 (brs, 1H), 11.7 (s, 1H), 6.76-6.65 (m, 3H), 6.41 (s, 1H), 4.28-4.21 (m, 4H), 3.61 (s, 2H)., 274910-19-9

As the paragraph descriping shows that 274910-19-9 is playing an increasingly important role.

Reference£º
Patent; Allergan, Inc.; US2006/69144; (2006); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Simple exploration of 274910-19-9

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.274910-19-9,(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,as a common compound, the synthetic route is as follows.,274910-19-9

Example 6 2-(1,4-benzodioxan-5-yl)acetic acid (6). To a solution of 5-hydroxymethyl-1,4-benzodioxan (8.0 g, 48 mmol) in dichloromethane (200 mL) was added two droplets of N,N-dimethylformamide and thionyl chloride (5.0 mL, 68 mmol) at room temperature. After the resulting solution was boiled under reflux for 1 h and subsequently cooled to room temperature water (100 mL) was added. The phases were separated and the organic phase was dried (MgSO4) and the solvents evaporated in vacuo. A solution of the remaining oil (8.5 g, 46 mmol) was added to a mixture of sodium cyanide (5.0 g, 102 mmol) and N,N-dimethylformamide (100 mL) at room temperature. After stirring for 16 h at room temperature ice was added and the resulting slurry was extracted with diethyl ether (2*250 mL). The collected organic phases were washed with saturated calcium chloride, dried (Na2SO4) and the solvents were evaporated in vacuo. A mixture of the remaining oil (6.0 g, 34 mmol), ethanol (200 mL), sodium hydroxide (6.0 g) and water (6 mL) was boiled under reflux for 16 h. After evaporation of the solvents in vacuo, water (200 mL) was added and the resulting slurry was extracted with diethyl ether (2*200 mL). The collected organic phases were washed with brine, dried (Na2SO4) and the solvents were evaporated in vacuo affording 4.0 g (43%) of the title compound as an oil: 1H NMR (CDCl3) delta 3.65 (s, 2H), 4.15-4.30 (m, 4H), 6.70-6.85 (m, 3H).

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various fields.

Reference£º
Patent; H. Lundbeck A/S; US2002/32205; (2002); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Simple exploration of 274910-19-9

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.274910-19-9,(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,as a common compound, the synthetic route is as follows.

A solution of 20 (3.75 g, 32.3 mmol) in diethyl ether (80 mL) was cooled to 0 C and phosphorous tribromide (3.67 mL, 38.8 mmol) was added dropwise. The solution was stirred at 0 C for 10 min, then at r.t. for 1 h. Water (10 mL) was added cautiously to quench the excess of reagent and the mixture was diluted with diethyl ether and washed with water (3 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 21 as a brown solid (4.61 g, 62%). 1H NMR (CDCI3) delta 6.91-6.77 (m, 3H), 4.52 (s, 2H), 4.35-4.33 (m, 2H), 4.29-4.27 (m, 2H). Found: [M+H- Br]=149.5., 274910-19-9

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various.

Reference£º
Patent; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; UPTON, Anna, Marie; COOPER, Christopher, Blair; MARCEL, Koenraad, Jozel Lodewijk; GUILLEMONT, Jerome, Emile Goerges; VAN DEN BROECK, Walter Marcel, Mathilde; PALMER, Brian, Desmond; MA, Zhenkun; (186 pag.)WO2017/155909; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Some tips on 274910-19-9

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various.

274910-19-9, (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,274910-19-9

N5-Cyclobutyl-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-d icarboxamide (50 mg, 0.201mmol), (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol (50.0 mg, 0.301 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.166 mL, 0.632 mmol) were combined in toluene (1.5 mL)and the reaction mixture heated in a 5 mL microwave vial on a Biotage Initiator microwave at 120C for 30 mm. The reaction mixture was poured onto water (20 mL), and extracted with ethylacetate (3 x 10 mL). The combined organic portions were evaporated in vacuo to yield the crude product as a brown oil. The product was loaded in dichloromethane onto a 25 g SNAP silica cartridge and purified via Biotage 5P4 flash chromatography, eluting from 50 – 100 % ethyl acetate/cyclohexane. The relevant fractions were combined and evaporated in vacuo – yielding 76mg of product. The sample was dissolved in MeOH/DMSO (1 mL, 1:1) and purified by MDAP (Formic). The solvent was evaporated in vacuoto give the required product – N5-cyclobutyl-1-((2,3- dihyd robenzo[b] [1,4]d ioxin-5-yl)methyl)-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-dicarboxamide(40 mg, 0.096 mmol, 47.7 % yield).LCMS (2 mm Formic): Rt = 0.95 mi [MH] = 398.1.

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Some tips on 274910-19-9

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various.

274910-19-9, (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(3) 2,3-ethylenedioxybenzyl chloride 4.3 g of 2,3-ethylenedioxybenzyl alcohol was dissolved in 50 ml of dry dichloromethane. Then, 2.1 ml of dry pyridine was dropwise added thereto, and 3.8 ml of thionyl chloride was gradually added under cooling. The reaction solution was returned to room temperature and then the reaction solution was refluxed for 3 hours on a hot water bath at 60 C. The reaction solution was concentrated under reduced pressure to obtain a syrup, which was then dissolved in 300 ml of ethyl acetate. The solution was washed with 200 ml of 0.1N hydrochloric acid and then twice with 200 ml of a saturated sodium chloride aqueous solution. Then, the solution was dried over anhydrous magnesium sulfate. The inorganic salt was removed by filtration, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane/ethyl acetate=60/1) to obtain 4.0 g of the above identified compound as syrup. Rf: 0.64 (n-hexane/ethyl acetate=2/1)., 274910-19-9

274910-19-9 (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol 2776182, abenzodioxans compound, is more and more widely used in various.

Reference£º
Patent; Banyu Pharmaceutical Co., Ltd.; US5122523; (1992); A;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Introduction of a new synthetic route about 274910-19-9

With the rapid development of chemical substances, we look forward to future research findings about 274910-19-9

(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, cas is 274910-19-9, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.

2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol (533 mg, 3.20 mmol) is dissolved in chloroform (4 mL), pyridine (0.11 mL) and thionyl chloride (0.7 mL, 9.7 mmol) is added little by little and the mixture is stirred at room temperature for 1 hour. The reaction solution is added with water and extracted with dichloromethane, and the organic layer is washed with aqueous sodium hydrogen carbonate solution. The organic layer is dried, the solvent is distilled off under reduced pressure, and pale yellow liquid of 578 mg is obtained in 97% yield.

With the rapid development of chemical substances, we look forward to future research findings about 274910-19-9

Reference£º
Patent; KANTO KAGAKU KABUSHIKI KAISHA; ABE, Jiro; INAGAKI, Yuki; SUGA, Takayoshi; NAGASAWA, Hiroto; US2020/131193; (2020); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Analyzing the synthesis route of 274910-19-9

The synthetic route of 274910-19-9 has been constantly updated, and we look forward to future research findings.

274910-19-9, (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2,3-Dihydro-1,4-benzodioxin-5-ylinethanol (1.01 g, 6.07 mmol) was dissolved in methylene chloride (60 mL). Manganese dioxide (3.81 g, 43.8 mmol) was added, and then the mixture was stirred in a nitrogen atmosphere at room temperature for 24 hours. Manganese dioxide was separated by filtration and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane = 1/4) to give the target compound (835 mg, yield: 84%) as a colorless oil. 1H-NMR (CDCl3, 400MHz):delta ppm: 4.32-4.34 (2H, m), 4.38-4.41 (2H, m), 6.91 (1H, t, J=7.8Hz), 7.10 (1H, dd, J=1.6, 7.8Hz), 7.40 (1H, dd, J=1.6, 7.8Hz). MS (EI) m/z: 164.0468 (M+)

The synthetic route of 274910-19-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP1914229; (2008); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Brief introduction of 274910-19-9

The synthetic route of 274910-19-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.274910-19-9,(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,as a common compound, the synthetic route is as follows.

[00209j A mixture of Intermediate 1(500mg, 1.5 mmol), (2,3-dihydrobenzo[b][1,4] dioxin-5-yl)methanol (380 mg, 2.3 mmol) and Cs2CO3 (1000 mg, 3.1 mmol) in DMSO (5 mL) was stirred for 2 days at 120 C. The reaction mixture was diluted with water andbrine (1:1, 50 mL) and extracted with EtOAc (2 x 30 mL). The combined organics were washed with brine, dried over Na2504 and concentrated in vacuo. The crude product was purified by column chromatography to yield the Example 2A (400 mg, 0.97 mmol, 63% yield), as a brown oil. MS (ESI) m/z 412.2 (M+H).

The synthetic route of 274910-19-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WURTZ, Nicholas R.; VIET, Andrew Quoc; SHAW, Scott A.; VOKITS, Benjamin P.; KICK, Ellen K.; VALENTE, Meriah Neissel; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; JUSUF, Sutjano; (140 pag.)WO2016/40417; (2016); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Brief introduction of 274910-19-9

The synthetic route of 274910-19-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.274910-19-9,(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,as a common compound, the synthetic route is as follows.

2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol (533 mg, 3.20 mmol) is dissolved in chloroform (4 mL), pyridine (0.11 mL) and thionyl chloride (0.7 mL, 9.7 mmol) is added little by little and the mixture is stirred at room temperature for 1 hour. The reaction solution is added with water and extracted with dichloromethane, and the organic layer is washed with aqueous sodium hydrogen carbonate solution. The organic layer is dried, the solvent is distilled off under reduced pressure, and pale yellow liquid of 578 mg is obtained in 97% yield.

The synthetic route of 274910-19-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KANTO KAGAKU KABUSHIKI KAISHA; ABE, Jiro; INAGAKI, Yuki; SUGA, Takayoshi; NAGASAWA, Hiroto; US2020/131193; (2020); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem