Heterocyclic Building Blocks-benzodioxan

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.2879-20-1,1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,as a common compound, the synthetic route is as follows.

A mixture of Intermediate 5 (210 mg, 1.04 mmol) and 6-acetyl-l,4-benzodioxane (CAS: 2879-20-1; 223 mg, 1.25 mmol) in Ti^Pr^ (3.1 mL, 10.4 mmol) were stirred at 75 C under N2 atmosphere for 4 h. The reaction mixture was cooled to 0 C under N2 atmosphere and 1 ,2-dichloroethane (1 mL), MeOH (15 mL) and sodium boro hydride (1 18 mg, 3.13 mmol) were sequentially added. The reaction mixture was allowed to warm to rt and further stirred at rt for 3 h. Water and DCM were added. The mixture was filtered through a celite pad and the volatiles were evaporated in vacuo. The residue thus obtained was taken up in DCM and HCl (lmL, 4N in 1,4-dioxane) was added. The volatiles were evaporated in vacuo and the resulting residue was treated with Et20 to give a solid that was filtered and dried to yield product 33 as hydrochloric acid salt (29 mg, 7% yield).

As the paragraph descriping shows that 2879-20-1 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; TRABANCO-SUAREZ, Andres, Avelino; MARTINEZ VITURRO, Carlos, Manuel; TRESADERN, Gary, John; ALCAZAR-VACA, Manuel, Jesus; (126 pag.)WO2018/109198; (2018); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

2879-20-1, 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A series of sixteen novel 1, 4-benzodioxane-based thiosemicarbazones(3a-p) was synthesized by reacting appropriatethiosemicarbazide (1a-p) (5 mmol) and 1, 4-benzodioxan-6-ylmethyl ketone (2) (5 mmol) in methanol (15 mL) using glacialacetic acid (1e2 drops) as catalyst. Reflux at 80 C for 6 h wascarried out and the product formation and the reaction completion were examined by thin layer chromatography. Upon completion,the reaction mixturewas allowed to cool at r.t and the solid productwas collected by suction filtration followed by washing with hotmethanol and then dried in vacuum. Finally, the target thiosemicarbazonesderivatives were recrystallized from chloroformmethanolmixture (1:1) in good to excellent yields. The X-raymeasurements were read by mounting a 3m single crystal on agreased MiTe Gen loop and was inspected through thediffractometer (Bruker D8 Venture APEX diffractometer) at 296 (2)K by means of graphite-monochromated MoeK a radiation(l 0.71073 A); diffractometer was complimented with an areadetector (Photon 100 CCD) along with a cooler (Oxford Cryostream).APEX-II software was used to collect Data [41] and SAINTwas operated for integration [42] The SADABS (multi-scanapproach) was used for correction in absorption [43]. and intrinsicphasing (SHELXT)was employed to the solve the structure [44]. Fullleast squares refinement of all detected reflections were used todetermine the final cell constants and assign positions of all atomsother than H to the consequential difference maps via refinementagainst F2. Whereas H atoms were assigned location and addedagainst F2 and were refined by riding model. SHELXL-97 wasimplemented to refine anisotropically [45]. The CCDC (CSD depositionnumbers 1874544) of the structure has been deposited. Thedetailed characterization of compounds 3a e 3p are given insupporting informations.

The synthetic route of 2879-20-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Shehzad, Muhammad Tariq; Khan, Ajmal; Islam, Muhammad; Hameed, Abdul; Khiat, Mohammed; Halim, Sobia Ahsan; Anwar, Muhammad U.; Shah, Syed Raza; Hussain, Javid; Csuk, Rene; Khan, Samra; Al-Harrasi, Ahmed; Shafiq, Zahid; Journal of Molecular Structure; vol. 1209; (2020);,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3663-80-7,2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

To a stirred solution of l,4-benzodioxane-2-carboxylic acid (9.0 g, 50 mmol), HATU (19.0 g, 50 mmol) and DIPEA (35 mL) in DMF (100 mL) was added (R)-1-phenylethanamine (6.4 mL, 50 mmol) at 22 ¡ãC, and the mixture was allowed to stir at 22 ¡ãC for 16 hrs. Water (200 mL) was added, and the mixture was stirred at 22¡ãC for 10 hrs. The aqueous layer was decanted, and the sticky residue was washed with water carefully, dried, and purified by flash chromatography to give (R)-N-((R)-l-phenylethyl)-2,3-dihydrobenzo [bj [1 ,4j dioxine-2-carboxamide (2) 5.3 g (37 percent) and (S)-N-((R)- 1 -phenylethyl)-2,3 – dihydrobenzo[bj[1,4jdioxine-2-carboxamide (3) 5.7 g (40 percent). 2: ?H NMR (500 MHz, CDC13) 7.40?7.26 (m, 5H), 6.96 ? 6.84 (m, 4H), 6.79 (d, J= 7.2 Hz, 1H), 5.22?5.10 (m, 1H), 4.64 (dd, J= 7.5, 2.6 Hz, 1H), 4.56 (dd, J= 11.4, 2.6 Hz, 1H), 4.17 (dd, J= 11.4, 7.6 Hz, 1H), 1.47 (d, J= 6.9 Hz, 3H). ?3C NMR (125 MHz, CDC13) 166.1, 143.3, 142.4, 141.6, 128.8, 127.6, 126.2, 122.4, 121.9, 117.6, 117.1, 73.1, 65.5, 48.6, 21.7. APCI-MS mlz: 284 (M+H)t 3: ?H NMR (500 MHz, CDC13) 7.38 ? 7.27 (m, 3H), 7.26 ? 7.21 (m, 2H), 7.05 ?7.00 (m, 1H), 6.99 ? 6.92 (m, 3H), 6.85 (d, J = 6.7 Hz, 1H), 5.29 ? 5.20 (m, 1H), 4.77 (dd, J =7.3, 2.6 Hz, 1H), 4.59 (dd, J= 11.4, 2.7 Hz, 1H), 4.22 (dd, J= 11.4, 7.3 Hz, 1H), 1.61 (d, J= 6.9Hz, 3H). ?3C NMR (125 MHz, CDC13) 166.2, 143.3, 142.5, 141.5, 128.7, 127.4, 125.8, 122.5,121.9, 117.7, 117.1, 73.2, 65.4, 48.4, 21.9. APCI-MS mlz: 284 (M+H)t

The synthetic route of 3663-80-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NORTHWESTERN UNIVERSITY; KRAINC, Dimitri; SILVERMAN, Richard, B.; ZHENG, Jianbin; (84 pag.)WO2019/27765; (2019); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2879-20-1,1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,as a common compound, the synthetic route is as follows.

General procedure: In a typical reaction, acetophenone (0.4 mmol) and I2 (0.4 mmol)was stirred in DMSO (1 mL) at 60C for 6 h. After the mixture was cooled to room temperature and subsequently, 2-methylindol(0.2 mmol), sesamol (0.2 mmol) were added to the reaction solutionalong with PTSA (0.04 mmol, 20 mol %). The mixture was then stirred at 80C for 3 h. At the end of the reaction,water (10 mL)was added and then extracted with EtOAc (310 mL). The acquired organic phase was combined and dried with anhydrous Na2SO4.The volatile components were removed under reduced pressure.The product was obtained by isolation with preparative TLC (elutingsolution: petroleum ether/dichloromethane1/2 (v/v)). Tests for substrate scope and the reaction of using other nucleophiles were all performed according to an analogous procedure. Whena 10 mmol scale reaction was conducted, the product was isolated by silica column chromatography.

2879-20-1 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone 76143, abenzodioxans compound, is more and more widely used in various.

Reference£º
Article; Cheng, Cheng; Liu, Changhui; Gu, Yanlong; Tetrahedron; vol. 71; 42; (2015); p. 8009 – 8017;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

3663-80-7, 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. 4.5.29 (3-(4-Bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanone (D14) White crystal, mp: 199-201 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.21-3.27 (m, 1H), 3.82-3.88 (m, 1H), 4.45-4.66 (m, 2H), 5.61-5.66 (m, 1H), 5.80-5.84 (m, 1H), 6.86-6.88 (m, 3H), 7.02-7.23 (m, 4H), 7.47 (m, 3H), 7.74-7.77 (d, J = 7.5 Hz, 2H). MS (ESI): 481.05 (C24H19BrFN2O3, [M+H]+). Anal. Calcd for C24H18BrFN2O3: C, 59.89; H, 3.77; Br, 16.60; F, 3.95; N, 5.82; O, 9.97. Found: C, 59.72; H, 3.75; N, 5.83.

The synthetic route of 3663-80-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yang, Yu-Shun; Li, Qing-Shan; Sun, Shuai; Zhang, Yan-Bin; Wang, Xiao-Liang; Zhang, Fei; Tang, Jian-Feng; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6048 – 6058;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2879-20-1,1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,as a common compound, the synthetic route is as follows.

General procedure: 1a-j (0.0299 – 0.0532 g, 0.299 mmol, 1 eq.), 2a-d (0.0166 – 0.228 g, 0.224 mmol, 0.75 eq.), FeCl3 (0.0145 g, 0.0897 mmol, 0.3 eq.), (NH4)2S2O8 (0.1363 g, 0.598 mmol, 2 eq.), and DCE / CCl4 (0.75 mL, 1 / 1) were stirred in Schott culture tubes (H ¡Á diam. 160 mm ¡Á 16 mm) at 120 C for 3 h. Further, after adding a solution of 2a-d (0.055 – 0.0763, 0.0748 mmol, 0.25 eq.) and DCE / CCl4 (0.08 mL, 1 / 1), the reaction mixture was stirred at 120 C for 3 h (3 times at 3-hour intervals). Next it was stirred at 120 C for 12 h. The yields of 3a-f,a-d were determined by 1H NMR (CDCl3) after the filtration of the reaction mass through a thin pad (0.4 – 0.5 cm) of silica gel (0.015 – 0.040 mm) using 20 mL of DCM and evaporation of solvent in vacuum. Products 3c,b and 3d,a-d were isolated by gradient flash chromatography (eluent: petroleum ether / ethyl acetate).

The synthetic route of 2879-20-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Arzumanyan, Ashot V.; Tetrahedron Letters; vol. 58; 50; (2017); p. 4667 – 4671;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem