Heterocyclic Building Blocks-Benzoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4570-41-6,Benzo[d]oxazol-2-amine,as a common compound, the synthetic route is as follows.

Step 1:To a solution of 4-pyridyl acetic acid hydrochloride (521 mg, 3 mmol) and 2-aminobenzoxazole (402 mg, 3 mmol) in CH2Cl2 (50 mL) was added DMAP (110 mg, 0.9 mmol) and EDC.HCl (690 mg, 4 mmol).The reaction mixture was stirred at room temperature over night.The reaction mixture was concentrated in vacuo.Purification by chromatography (silica, 2-5percent methanol/CH2Cl2 gradient) afforded N-benzooxazol-2yl-2-pyridin-4-yl-acetamide (228 mg, 30percent): 1H NMR (300 MHz, METHANOL-d4) delta ppm 5.05 (br. s., 2H) 7.19-7.35 (m, 2H) 7.39-7.49 (m, 3H) 7.54 (dt, J=7.25, 1.08 Hz, 1H) 8.39-8.56 (m, 2H).

4570-41-6 Benzo[d]oxazol-2-amine 20707, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; Brotherton-Pleiss, Christine E.; Walker, Keith A. M.; US2012/149718; (2012); 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.

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]+.

As the paragraph descriping shows that 22876-19-3 is playing an increasingly important role.

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

128156-54-7, Methyl benzo[d]oxazole-4-carboxylate is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure.

The synthetic route of 128156-54-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sasmal, Swarnendu; Sen, Indira; Hall, Roger G.; Pal, Sitaram; Tetrahedron Letters; vol. 56; 11; (2015); p. 1374 – 1377;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.136992-95-5,Benzo[d]oxazol-7-amine,as a common compound, the synthetic route is as follows.

A mixture of benzooxazol-7-amine (135 mg, 1.01 mmol, Astrazeneca, PCT Appl. WO2003053960), 2.4-dichloropyrimidine (150 mg, 1.01 mmol), DBU (0.197 ml, 1.32 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (58 mg, 0.1 mmol, also named xantphos) and tris(dibenzylideneacetone)dipalladium(0) (58 mg, 0.1 mmol, also named Pd2dba3) in dioxane (3 ml) under argon was irradiated in a Personal Chemistry EMRYS Optimizer EXP microwave synthesisor at 110 C. for 10 minutes. After cooling and evaporation of the solvents, the residue was dissolved in DCM and purified by chromatography on silica gel (eluant: 30% to 60% EtOAc in petroleum ether) to give N-(2-chloropyrimidin-4-yl)benzooxazol-7-amine (88 mg, 35%) as a beige solid. Mass spectrum: MH+ 247

As the paragraph descriping shows that 136992-95-5 is playing an increasingly important role.

Reference£º
Patent; AstraZeneca AB; US2011/46108; (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.81282-60-2,7-Aminobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.

4.91 g (32.7 mmol) of the anilin was suspended in 75 ml of 48% of HBr/water, while it was cooled to -5 C. Subsequently 2.27 g (33 mmol) of sodium nitrite dissolved in 4 ml of water, were added dropwise during 15 minutes. Stirring was continued at 0 C. for 15 minutes. Subsequently, the reaction mixture was added, in one time, to a 0 C. solution of 2.42 g (16.9 mmol) CuBr in 20 ml of 48% HBr/water. After 30 minutes the reaction mixture was heated to 85 C. for one hour, after which it was allowed to reach room temperature, stirring was continued for 14 hours. To the mixture diethyl ether and water were added, after shaking the organic layer was isolated which was washed with water. The organic layer, together with some silica, was concentrated in vacuo, and the residue was put on top of a flash chromatography column (SiO2) using Et2O/petroleum ether (1/1), and later on pure Et2O as the eluent. The combined product containing fractions yielded after concentration in vacuo 3.3 g (47%) of the desired corresponding bromo product.

81282-60-2 7-Aminobenzo[d]oxazol-2(3H)-one 11147814, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122189; (2006); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

132244-31-6, 5-Bromobenzo[d]oxazole is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a flame-dried reaction tube was added 1,3-azoles (0.5 mmol, 1.0 eq), 1,10-phenoline (0.5 mmol, 1.0 eq), LiOtBu (1.0 mmol, 2.0 eq), CuBr2 (0.10 mmol, 0.2 eq) and iodine (0.75 mmol, 1.5 eq). Dry 1,4-dioxane (2 mL) was added to the mixture and the mixture was heated to 80C by putting the reaction tube to a preheated oil bath until the products were not increased. The mixture was cooled to room temperature and filtered through a short pad of silica gel. The silica gel was washed with EtOAc (20 mL) and the combined the organic phase was concentrated under reduced pressure to give a residue which was purified by silica gel column chromatography to afford the iodination product.

The synthetic route of 132244-31-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhao, Xia; Ding, Fang; Li, Jingyu; Lu, Kui; Lu, Xiaoyu; Wang, Bin; Yu, Peng; Tetrahedron Letters; vol. 56; 3; (2015); p. 511 – 513;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.81282-60-2,7-Aminobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.

4-trifluoromethylphenylacetic acid (453 mg, 2.2 mmol) was dissolved in 20 ml of THF and at 0C DEPC (0.43 ml, 1.3equiv) and amine lc (400 mg, 2.66 mmol) were added to the solution. The mixture was warmed at 80C overnight, then 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 using AcOEt 3 /petroleum ether 7 as eluant gave 340 mg of a white solid. Yield = 46% 1HNMR (DMSO, 200 MHz) delta 3.86 (2H, s), 6.86 (1H, d), 7.06 (1H, t), 7.58 (3H, m), 7.70 (2H, d, J = 8.4 Hz), 10.32 (1H, bs), 8.73 (1H, bs), 1 1.80 (1H, bs); [M+1] 337.2 (C 16H11F3N2O3 requires 336.3).

The synthetic route of 81282-60-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (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.

Example 103-[1-(5-chloro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (One Enantiomer Isolated) To a solution of 5-chloro-1,3-benzoxazole-2-thiol (0.50 g, 2.7 mmol, Aldrich) in toluene (10 mL) was added thionyl chloride (0.59 mL, 8.1 mmol) followed by a drop of DMF. The reaction was heated to reflux for 30 min and the solvent removed in vacuo. A portion of this crude product (17 mg) and 3-pyrrolidin-3-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (20.0 mg, 0.0457 mmol; enantiomer 2 from Example 9, Step 2b) were dissolved in 1,4-dioxane (0.40 mL) and N,N-diisopropylethylamine (16 microL, 0.091 mmol) was added. The mixture was heated to 70 C. for 1.5 h. The solvent was removed in vacuo and the residue was sequentially stirred with 50% TFA/DCM for 1.5 h, concentrated, then stirred with 0.3 mL EDA in methanol for 30 min. Purification via preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) afforded product. 1H NMR (400 MHz, d6-DMSO): delta 12.13 (br s, 1H), 8.88 (s, 1H), 8.68 (s, 1H), 8.43 (s, 1H), 7.60 (d, 1H), 7.41 (d, 1H), 7.31 (d, 1H), 7.02-6.97 (m, 2H), 4.86 (dt, 1H), 3.86 (dd, 1H), 3.68-3.59 (m, 1H), 3.54-3.28 (m, 4H), 3.03-2.90 (m, 1H), 1.77-1.67 (m, 2H); LCMS (M+H)+: 459.0, 461.0.

22876-19-3 5-Chlorobenzo[d]oxazole-2(3H)-thione 708870, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

59-49-4, 2-Benzoxazolinone is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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]+.

59-49-4 2-Benzoxazolinone 6043, abenzoxazole compound, is more and more widely used in various.

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

59-49-4, 2-Benzoxazolinone is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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]+.

59-49-4 2-Benzoxazolinone 6043, abenzoxazole compound, is more and more widely used in various.

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