Day: September 11, 2020

The benzoxazole compound, name is 7-Aminobenzo[d]oxazol-2(3H)-one,cas is 81282-60-2, mainly used in chemical industry, its synthesis route is as follows.,81282-60-2

To a mixture of 14.9 g N-methyldiethanolamine (3), 44.5 g triethylamine and 120 ml methyl ethyl ketone (MEK) a mixture of 51.6 g methanesulfonic anhydride and 100 ml MEK was dosed at 0 C. Subsequently 14.5 g methanesulfonic acid was dosed at 0 C. After which, 14.5 g 7-amino-2(3H)-benzoxazolone (2) was added and the mixture was heated to reflux followed by a reflux period of 48 hours during which the product crystallized. The product was filtered off after cooling to 0 C. and washed with MEK. The product was dried at 50 C. and 100 mbar to constant weight. The overall yield of this step was about 67% (crude on crude).

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Reference£º
Patent; Rheenen, Jeroen Van; Muijselaar, Wilhelmus G.H.M.; Teunissen, Hendrik; US2011/86862; (2011); A1;,
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The benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one,cas is 19932-85-5, mainly used in chemical industry, its synthesis route is as follows.,19932-85-5

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

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Reference£º
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
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The benzoxazole compound, cas is 22876-19-3 name is 5-Chlorobenzo[d]oxazole-2(3H)-thione, mainly used in chemical industry, its synthesis route is as follows.,22876-19-3

INVENTIVE EXAMPLE 24 2-(4-Methyl-1-piperazinyl)-5-trifluoromethylbenzoxazole 2-Mercapto-5-trifluoromethylbenzoxazole (200 mg) which has been obtained in the same manner as described in Reference Example 1 was dissolved in chloroform (10 ml), and the solution was mixed with N-methylpiperazine (0.5 ml) and heated overnight under reflux. The solvent was evaporated under a reduced pressure, the resulting residue was mixed with water and then the thus precipitated solid matter was collected by filtration to obtain the title compound 2-(4-methyl-1-piperazinyl)-5-trifluoromethylbenzoxazole (134 mg). 1 H-NMR (CDCl3): delta 2.36 (3 H, s), 2.54 (4 H, t), 3.75 (4 H, t), 7.30 (2 H, d), 7.57 (1 H, s); LCMS: m/z 286 (M+ +1)

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Reference£º
Patent; Meiji Seika Kaisha, Ltd; Koichi Shudo; US6037342; (2000); A;,
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The benzoxazole compound, cas is 151230-42-1 name is 6-Bromo-2-methylbenzo[d]oxazole, mainly used in chemical industry, its synthesis route is as follows.,151230-42-1

[0510] Compound 71a: To a mixture of Comp-8b (0.47 g, 2.35 mmol) and 6-bromo-2- methylbenzo[d]oxazole (0.5 g, 2.35 mmol) in was added 7-BuOK (2 mL, IM in THF) at 0 C and the reaction mixture was stirred at RT for 12 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated under reduced pressure and the crude obtained was purified by column chromatography (silica, 230-400 mesh, 40-50% EtOAc in hexane) to afford (E)-6-bromo-2-(2-(2,5-dimethyl-l-phenyl-lH- pyrrol-3-yl)vinyl)benzo|i ]oxazole (71a; 0.3 g, 32%) as a yellow solid.

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Reference£º
Patent; ALPINE ANDROSCIENCES, INC.; PATIL, Santhosh N.; SARMA, Bugga VNBS; (148 pag.)WO2019/152731; (2019); A1;,
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The benzoxazole compound, cas is 5676-60-8 name is 2-Methylbenzo[d]oxazol-6-amine, mainly used in chemical industry, its synthesis route is as follows.,5676-60-8

EXAMPLE 4 Compound No. 4 N-[6-(2,6-dichlorophenyl)-2-[(2-methyl-6-benzoxazolyl)amino]pyrido[2,3-d]pyrimidin-7-yl]-N’-(1,1-dimethylethyl)urea 210 mg of the amine of preparation 20 in Table 2 and 562 mg of the urea of preparation 1 in Table 1 are heated for 8 hours at 45 C. in 20 ml of ethanol containing 0.02 ml of concentrated HCl. After concentration under reduced pressure, the residue is chromatographed on silica gel, the eluent being CHCl3/MeOH: 98/2 (v/v). 300 mg of product in the form of a yellow solid are isolated. MH+: 536.

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Reference£º
Patent; SANOFI-AVENTIS; US2008/176874; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.701-16-6,5-Fluoro-2-methylbenzo[d]oxazole,as a common compound, the synthetic route is as follows.,701-16-6

General procedure: The SBOs were prepared by the base-catalysed condensation of the appropriate 5-halogeno-2-methylbenzoxazole with the requisite aromatic aldehyde under phase transfer conditions. In a typical experiment, equimolar quantities (5 mmol) of the starting materials were dissolved in dichloromethane (20-50 ml) in the presence of benzyltriethylammonium chloride (3 mmol) and stirred magnetically under a nitrogen atmosphere as an aqueous solution of sodium hydroxide (50%, w/v, 5 ml) was added dropwise over a period of 10 min. After being stirred for 2-36 h until analytical thin layer chromatography indicated that the reaction was complete, the mixture was diluted with water (50 ml) and the SBO was extracted with dichloromethane (3¡Á20 ml), dried (MgSO4), filtered, evaporated under reduced pressure and recrystallized from aqueous methanol or ethanol.

As the paragraph descriping shows that 701-16-6 is playing an increasingly important role.

Reference£º
Article; Ayrton, Stephen T.; Panova, Jekaterina; Michalik, Adam R.; Martin, William H.C.; Gallagher, Richard T.; Bowen, Richard D.; International Journal of Mass Spectrometry; vol. 345-347; (2013); p. 120 – 131;,
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19932-85-5, 6-Bromobenzo[d]oxazol-2(3H)-one is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Bromide 1 (12.8 g, 59.6 mmol) was dissolved in anhydrous THF (220 mL), and the solution was cooled to ?78 C. Solutions of MeMgBr (21.9 mL of a 3.0 M solution in Et2O, 65.6 mmol), sec-BuLi (50.4 mL of a 1.3 M solution in cyclohexane, 65.6 mmol), and 1,4-Cyclohexanedione mono-ethylene ketal (11.2 g, 71.5 mmol) in anhydrous THF (10 mL) were added sequentially at 30-minute intervals. After the final addition, the reaction mixture was allowed to warm to room temperature. The reaction was quenched by the addition of 1N HCl (25 mL). The reaction mixture was diluted with EtOAc (500 mL), washed with saturated NaCl (250 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to provide a mixture of 2 and 3, as a brown oil.

19932-85-5, As the paragraph descriping shows that 19932-85-5 is playing an increasingly important role.

Reference£º
Patent; Nikam, Sham Shridhar; Scott, Ian Leslie; Sherer, Brian Alan; Wise, Lawrence David; US2003/236252; (2003); A1;,
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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, To a solution of 2,4-dichloropyrimidine (1 mmol) and 2-methyl-1,3-benzoxazol-5-amine (1 mmol) in 5ml EtOH was added Et3N (1 mmol). The reaction mixture was refluxed for 5 h. After removal of the solvent in vacuo and addition of H2O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-chloro pyrimidin-4-yl)-2-methylbenzo[d]oxazol-6-amine in a yield of 73%.

The synthetic route of 5676-60-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hutchison MediPharma Enterprises Limeted; US2008/255172; (2008); A1;,
Benzoxazole – Wikipedia
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The benzoxazole compound, cas is 5676-60-8 name is 2-Methylbenzo[d]oxazol-6-amine, mainly used in chemical industry, its synthesis route is as follows.,5676-60-8

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (163 mg, 0.723 MMOL) in dichloromethane (3 mL) was added pyridine (140 pL, 1.72 MMOL) and the mixture was stirred under N2 for 5 min, after which time 6-amino-2-methylbenzoxazole (102 mg, 0.688 MMOL) was added. The resulting mixture was stirred for 1 h at room temperature, then saturated NAHC03 solution was added (8 mL) and the mixture was extracted into ethyl acetate (15 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 (151 mg, 65%), single spot at Rf 0.50 (60: 40 hexane: ethyl acetate). mp 127.1-127. 5C, HPLC purity 97% (tR 2.05 min in 10% WATER-ACETONITRILE). 1H NMR (CDCl3) : O 7.85 (1H, dd, J=8.1, 1.1 Hz), 7.53 (1H, dd, J=8.1, 1.3 Hz), 7.45 (1H, d, J=8. 4 Hz), 7.27 (1H, d, J=2.2 Hz), 7.17 (1H, t, J=7.9 Hz), 6.93 (1H, s, N-H), 6.86 (1H, dd, J=8.4, 2.2 Hz), 2.71 (3H, s), 2.58 (3H, s). LCMS: 335.14 (M-). FAB-MS (MH+, C15H13CIN203S) : calcd 337.0413, found 337.0406.

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Reference£º
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Benzoxazole – Wikipedia
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The benzoxazole compound, cas is 19932-85-5 name is 6-Bromobenzo[d]oxazol-2(3H)-one, mainly used in chemical industry, its synthesis route is as follows.,19932-85-5

To a solution of 1-bromo-4-chlorobutane (2.17?mL, 18.7?mmol), K2CO3 (3.87?g, 28.04?mmol) in ACN (1?mL) was added dropwise at a solution of 6-bromo-3H-1,3-benzoxazol-2-one (1) in ACN (3?mL). The mixture was heated at 80?C for 12?h. The inorganics were removed by filtration and the solvent was evaporated. The residue was purified by column chromatography (cyclohexane/ethyl acetate), 9:1 (v:v)) to afford 6-bromo-3-(4-chlorobutyl)-1,3-benzoxazol-2-one as a white solid (1.2?g, 3.94?mmol). Mp 61.9-62.4?C. 1H NMR (300?MHz, CDCl3): delta 7.39 (d, J?=?1.8?Hz, 1H), 7.34 (dd, J?=?8.3, 1.8?Hz, 1H), 6.88 (d, J?=?8.3?Hz, 1H), 3.87 (t, J?=?6.8?Hz, 2H), 3.60 (t, J?=?6.1?Hz, 2H), 2.27-1.74 (m, 4H). 13C NMR (75?MHz, CDCl3): delta 154.1, 143.1, 130.2, 126.9, 114.8, 113.8, 109.2, 77.5, 77.0, 76.6, 44.0, 41.6, 29.2, 25.0. LCMS m/z calc for [M + ACN + H]+: 345.6, 347.6, found: 345.1, 347.1.

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Reference£º
Article; Gay, Marion; Evrard, Caroline; Descamps, Florian; Carato, Pascal; Renault, Nicolas; Coevoet, Mathilde; Eddarkaoui, Sabiha; Baud, Catherine; Larchanche, Paul-Emmanuel; Buee, Luc; El Bakali, Jamal; Vingtdeux, Valerie; Sergeant, Nicolas; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 104 – 125;,
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