Day: November 5, 2020

2-Benzoxazolinone, cas is 59-49-4, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,59-49-4

Step 1: N-Bromosuccinimide (26.6 g, 0.15 mol) was added to a stirred solution of 2-benzoxazolinone (20.0 g, 0.15 mol) in glacial acetic acid (220 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into H2O (1.2 L), and the white solid that formed was collected. Recrystallization from hot EtOH (300 mL) gave bromide 1 (22.1 g, 70%) as an off-white solid: mp 190-195 C.; IR (KBr): 3278, 1779, 1736, 1623 cm?1; 1H NMR (300 MHz, CD3OD): ?7.41 (d, J=2 Hz, 1H), 7.32 (dd, J=5, 2 Hz, 1H), 6.99 (d, J=5 Hz, 1H); CI MS (methane) (m/z): 215 [M+H]+.

As the rapid development of chemical substances, we look forward to future research findings about 59-49-4

Reference£º
Patent; Nikam, Sham Shridhar; Scott, Ian Leslie; Sherer, Brian Alan; Wise, Lawrence David; US2003/236252; (2003); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,5-Chlorobenzo[d]oxazole-2(3H)-thione,22876-19-3,Molecular formula: C7H4ClNOS,mainly used in chemical industry, its synthesis route is as follows.,22876-19-3

A mixture of 5-chloro-benzooxazole-2-thiol (4.00 g, 21.5 mmol, 1.0 equiv; commercially available from Aldrich) and ethyl 4-amino-1-piperidine carboxylate (4.9 g, 28.0 mmol, 1.3 equiv) in anhydrous DMAc (5 mL) was heated to 200 C. under microwave irradiation for 20 min. To the crude reaction mixture was added a conc. solution of sodium chloride (100 mL), the solution extracted with ethyl acetate (3¡Á100 mL) and the combined organic phases dried over MgSO4. Purification of the crude material with column chromatography on silica eluting with hexane/ethyl acetate (2:1?1:1) yielded 2.7 g (39%) of the title compound. 1H NMR (400 MHz, DMSO): delta 1.19 (t, J=7.1 Hz, 3H), 1.39-1.45 (m, 2H), 1.93-1.97 (m, 2H), 2.98 (br s, 2H), 3.77-3.78 (m, 1H), 3.91-3.95 (m, 2H), 4.04 (q, J=7.1 Hz, 2H), 7.00 (dd, J=8.4 Hz, J=2.1 Hz, 1H), 7.29 (d, J=2.1 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 8.19 (d, J=7.6 Hz, 1H). 13C NMR (100 MHz, DMSO): delta 14.53, 31.11, 42.07, 49.60, 60.63, 109.45, 115.10, 119.65, 127.78, 144.86, 146.71, 154.56, 162.50. MS (ISP): 324.1 [M+H]+.

With the synthetic route has been constantly updated, we look forward to future research findings about 5-Chlorobenzo[d]oxazole-2(3H)-thione,belong benzoxazole compound

Reference£º
Patent; Binggeli, Alfred; Christ, Andreas Dominik; Green, Luke Gideon Granville; Guba, Wolfgang; Maerki, Hans-Peter; Martin, Rainer Eugen; Mohr, Peter; US2006/205718; (2006); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.,19932-85-5

Intermediate 13: 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carbonitrile To a solution of 6-bromo benzoxazolinone (2 g, 9.4 mmol) in DMF (20 mL) was added CuCN (16.79 g, 188 mmol), and the reaction was stirred at 175 C. for 6 h. The reaction progress was monitored by TLC (100% EtOAc). The reaction was diluted with EtOAc (10 mL) and filtered through Celite brand filter agent. The organic layer was concentrated and purified by column chromatography (silica gel, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 158.9 (MH-).

With the complex challenges of chemical substances, we look forward to future research findings about 19932-85-5,belong benzoxazole compound

Reference£º
Patent; AMGEN INC.; BISWAS, Kaustav; CHEN, Jian J.; GORE, Vijay Keshav; HARRIED, Scott; HORNE, Daniel B.; KALLER, Matthew R.; MA, Vu Van; SHAM, Kelvin; ZHONG, Wenge; US2014/45855; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

5676-60-8, 2-Methylbenzo[d]oxazol-6-amine is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5676-60-8

The synthetic route for 1 was outlined in Scheme 1, and the detailed procedures were presented as follows: (a) To a solution of 2-amino-5-nitrophenol (7.70g, 50.0mmol) and pyridine (3.96g, 50.0mmol) in dry xylene (150mL) at 0C was added dropwise acetyl chloride (4.32g, 55.0mmol). The solution was stirred at ambient temperature for 2h. To above solution was added p-toluenesulfonic acid (1.72g, 10.0mmol), the solution was refluxed till no water was discharged. After cooling to room temperature, the solution was washed with water (100mL¡Á3) and a saturated solution of NaCl (50.0mL), respectively. The organic solution was collected and dried over Na2SO4, after evaporation of the solvent, the crude 2-methyl-6-nitrobenzoxazole (pale solid, 8.80g, 95% yield) was obtained for next step without purification. (b) To a solution of 13 2-methyl-6-nitrobenzoxazole (3.92g, 22.0mmol) in 14 methanol (60.0mL) at 70C was added 15 NH4Cl (11.77g, 220mmol) in 16 H2O (40.0mL) and Fe (4.48g, 80.0mmol). The mixture solution was stirred at 70C for 4h till the starting material disappeared (TLC detection). The mixture solution was cooled to ambient temperature and filtered, the solution was extracted with ethyl acetate (30.0mL¡Á3). The combined organic solution was dried over Na2SO4, after evaporation of the solvent, the crude 17 2-methylbenzoxazol-6-amine (2.77g, 85% yield) was obtained for next step reaction without purification. (c) To a solution of 2-methylbenzoxazol-6-amine (2.66g, 18.0mmol) in methanol (30.0mL) was added 18 formaldehyde (37%, 12mL, 144mmol) and 19 NaBH3CN (2.27g, 36.0mmol). The solution was stirred at ambient temperature for 36h till the starting material disappeared (TLC detection). The solution was poured into H2O (30.0mL), and the mixture solution was extracted with ethyl acetate (30.0mL¡Á3). The combined organic solution was dried over Na2SO4, the solution is concentrated and 20 2-methyl-6-(N, N-dimethylamino) benzoxazole (2.50g, 79% yield) is obtained by flash column chromatography (elute: petroleum ether / ethyl acetate=10 / 1, v/v, Rf =0.11).

As the paragraph descriping shows that 5676-60-8 is playing an increasingly important role.

Reference£º
Article; Qu, Cong; Gao, Zheng; Chen, Yi; Journal of Photochemistry and Photobiology A: Chemistry; vol. 361; (2018); p. 62 – 66;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO199,mainly used in chemical industry, its synthesis route is as follows.,701-16-6

[0589] Compound 82: To a stirred solution of Comp-82b (0.1 g, 0.66 mmol) in mixture of THF (5 mL) and ffiuOH (1 mL) was added r-BuOK (0.2 g, 1.98 mmol) and the reaction mixture was stirred for 10 min. Comp-50c(0.1 g, 0.66 mmol) was added portion wise and the reaction mixture was stirred at room temperature for 16 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was quenched with H20 (5 mL) and extracted with EtOAc (10 mL X 2). The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude. The crude obtained was purified by prep HPLC to afford (E)-2-(2-(l-cyclopentyl-2,5- dimethyl-lH-pyrrol-3-yl)vinyl)-5-fluorobenzo[d]oxazole (82; 0.08 g, 40%) as white solid. (1026) [0590] HPLC Purity: 99.8% (1027) [0591] MS (ESI) m/e [M+H]+ Rt %: 325.2/2.47/99.4% (1028) [0592] 1H NMR (400 MHz, DMSO- d6) delta 1.62- 1.64 (m, 2 H), 1.82- 1.84 (m, 4 H), 1.98 – 2.08 (m, 2 H), 2.24 (s, 3 H), 2.36 (s, 3 H), 4.54 – 4.67 (m, 1 H), 6.26 (s, 1 H), 6.50 (d, J=15.65 Hz, 1 H), 7.10 – 7.19 (m, 1 H), 7.46 (dd, J=8.80, 2.45 Hz, 1 H), 7.62 – 7.64 (m, 1 H), 7.67 (d, J=15.65 Hz, 1 H).

With the complex challenges of chemical substances, we look forward to future research findings about 5-Fluoro-2-methylbenzo[d]oxazole,belong benzoxazole compound

Reference£º
Patent; ALPINE ANDROSCIENCES, INC.; PATIL, Santhosh N.; SARMA, Bugga VNBS; (148 pag.)WO2019/152731; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.153403-53-3,2-Chloro-6-fluorobenzo[d]oxazole,as a common compound, the synthetic route is as follows.

Example 66: N-[(/5,25)-2-[(6-Fluoro-l<3-benzoxazol-2-vl)amino1cvclopentyl1-2<6- dimethoxybenzamide To a solution of N-((iS,2S)-2-aminocyclopentyl)-2,6-dimethoxybenzamide hydrochloride (Intermediate 11, 100 mg, 0.332 mmol) in dry DMSO (1 ml) was added 2-chloro-6- fluoro-l,3-benzoxazole (57 mg, 0.332 mmol) and DIPEA (0.17 ml, 0.997 mmol). The reaction was irradiated under microwave conditions at 150 C for 8 hours and, upon cooling, was partitioned between ethyl acetate and water. The organic portion was washed with water and brine, dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC (acetonitrile / water containing 0.1% ammonia) to afford the title compound.1H NMR (DMSO-i/6) delta ppm 1.47 - 1.75 (m, 4 H), 1.95 - 2.12 (m, 2 H), 3.57 (s, 6 H), 4.01 - 4.07 (m, 1 H), 4.23 - 4.30 ( m, 1 H), 6.57 - 6.66 (m, 2 H), 6.87 - 7.02 (m, 1 H), 7.13 - 7.26 (m, 2 H), 7.33 - 7.44 (m, 1 H), 7.92 - 8.20 (m, 2 H)MS ES+: 400 153403-53-3, 153403-53-3 2-Chloro-6-fluorobenzo[d]oxazole 14748832, abenzoxazole compound, is more and more widely used in various fields.

Reference£º
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 5-Bromobenzo[d]oxazole, cas is 132244-31-6 its synthesis route is as follows.,132244-31-6

To a mixture of 5-bromobenzo[Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

2-Methylbenzo[d]oxazole-6-carbaldehyde, cas is 864274-04-4, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,864274-04-4

Example 72; 5-(2-Methyl-benzooxazol-6-ylmethylene)-2-(2-piperidin-l-yl-ethylimino)-thiazolidi n-4-one; a) 5- (2-Methyl-benzooxazol-6-ylmethylene)-2-thioxo-thiazolidin-4-one; To the solution of rhodanine (1.21 g, 10 mmol) in ethanol (50 mL) was added 2-methyl-benzooxazole-6-carbaldehyde (1.61 mg, 10 mmol, 1 eq) followed by pyridine (1 mL). The reaction mixture was refluxed for 24 hours cooled to the room temperature. Solid was filtered to give 1.3 g (47 percent yield) of pure 5-(2-methyl-benzooxazol-6-ylmethylene)-2-thioXo-thiazolidin-4-one. lH-NMR (DMSO): No. 2.67 (s, 3H), 2.85 (s, 3H), 7.66 (dd, 1H, J=8.3 Hz, J’=1. 7 Hz), 7.82 (d, 1H, J=8.3 Hz), 8.00 (s, 1H), 8.02 (d, 1H, J=1.7 Hz). LC MS (m/e) = 277.0 (MH+). Rt = 2.02 min.

As the rapid development of chemical substances, we look forward to future research findings about 864274-04-4

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/82901; (2005); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 4-Aminobenzo[d]oxazol-2(3H)-one, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 81900-93-8, its synthesis route is as follows.,81900-93-8

Example 30: 1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Amine 2b (289 mg, 1.2 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (356 mg, 1.2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (180 mg, 1.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 100mg of a white solid. Yield = 20% 1HNMR (DMSO, 200 MHz) delta 1.94 (4H, m), 3.23 (4H, m), 4.67 (2H, d, J = 5.6 Hz), 6.55 (2H, dd, J = 8.8 Hz, J’ = 1.2 Hz), 7.05 (1H, t, J = 8.2 Hz), 7.17 (2H, d, J = 7.2 Hz), 7.46 (1H, d), 9.98 (1H, t), 11.53 (1H, bs), 11.80 (1H, bs); [M+1] 421.2 (C20H19F3N4O3 requires 420.39).

With the complex challenges of chemical substances, we look forward to future research findings about 4-Aminobenzo[d]oxazol-2(3H)-one

Reference£º
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,as a common compound, the synthetic route is as follows.

22876-19-3, General procedure: A mixture of intermediate compound N-(3-(1H-tetrazole-5-yl) phenyl)-2-chloroacetamideand benzo[d]oxazole-2-thiol or benzo[d]thiazole-2-thiol or 2-mercapto benzimidazoles in anequimolar amount were taken and refluxed with acetone (20 mL) in the presence of K2CO3for 24 hr. The reaction was monitored by TLC and on completion of the reaction, an excessof solvent was evaporated at room temperature and the reaction mixture was diluted withwater (about 200 mL). The diluted hydrochloric acid was added to precipitate the productwhich was further filtered and thoroughly washed with cold water.

The synthetic route of 22876-19-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Maheshwari, Neelesh; Karthikeyan, Chandrabose; Bhadada, Shraddha V.; Verma, Amit K.; Sahi, Chandan; Moorthy, N.S. Hari Narayana; Trivedi, Piyush; Bioorganic Chemistry; vol. 92; (2019);,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem