Category: benzoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59-49-4,2-Benzoxazolinone,as a common compound, the synthetic route is as follows.

Step 1: To a solution of benzoxazolinone (20 g, 0.148 mol) in 220 mL glacial acetic acid was added N-bromosuccinimide (NBS, 26.36 g, 0.148 mol), and the reaction mixture was stirred at room temperature for 63 hours before pouring into 1500 mL water. The precipitated product was washed thoroughly with water upon collection and recrystallized from EtOH to give 6-bromo-3H-benzoxazol-2-one (9) (25.09 g, 79%): Theory: C, 39.28; H, 1.88; N, 6.54; Br, 37.33. Found: C, 39.36; H, 2.02; N, 6.36; Br, 37.43. MP 192-194 C.

The synthetic route of 59-49-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kornberg, Brian Edward; Lewthwaite, Russell Andrew; Manning, David; Nikam, Sham Shridhar; Scott, Ian Leslie; US2003/18021; (2003); A1;,
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19219-99-9, 5-Chloro-2-methylbenzo[d]oxazole is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparative Example 3; Step A; Commercially available 5-chloro-2-methylbenzoxazole (1.5 g), potassium cyanide (612 mg), dipiperidinomethane (720 muL), palladium diacetate (80 mg) and 1,5-bis-(diphenylphosphino)pentane (315 mg) were dissolved in dry toluene (20 mL), degassed and stirred at 160 C. in a sealed pressure tube under argon. After 24 h the mixture was diluted with ethyl acetate. The organic layer was washed with saturated ammonium chloride and brine, dried (MgSO4), concentrated and purified by column chromatography (silica, cyclohexane/EtOAc, 9:1 to 7:3) to afford the intermediate (372 mg; 26%) as a colourless solid. 1H-NMR (CDCl3) delta=2.63 (s, 3H), 7.48-7.58 (s, 2H), 7.90 (s, 1H).

The synthetic route of 19219-99-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ALANTOS PHARMACEUTICALS, INC.; US2007/155739; (2007); A1;,
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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

To a solution of 6-bromo-3H-1,3-benzoxazol-2-one (2.00 g, 9.35 mmol, Intermediate OY) in THF (50 mL) was added t-BuOK (1.26 g, 11.2 mmol). The reaction mixture was stirred at 0 C. for 0.5 hour. Subsequently, [1-[(4-methoxyphenyl)methyl]-2,6-dioxo-3-piperidyl] trifluoromethanesulfonate (4.81 g, 12.6 mmol, Intermediate IQ) in a solution of THF (30 mL) was added dropwise. The resulting reaction mixture was stirred at 20 C. for 0.5 hour under N2. On completion, the reaction mixture was quenched with saturated NH4Cl (100 mL), and extracted with ethyl acetate (100 mL). The combined organic layer was washed with brine (2¡Á100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (PE:EA:DCM=5:1:2) to give the title compound (3.75 g, 90% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.22-7.20 (d, J=8.0 Hz, 1H), 6.89-6.87 (d, J=8.0 Hz, 1H), 4.90-4.86 (m, 1H), 4.47-4.36 (m, 2H) 3.81 (s, 3H), 2.67-2.64 (m, 1H), 2.59-2.54 (m, 2H), 2.40-2.38 (m, 1H). LC-MS (ESI+) m/z 466.9 & 468.9 (M+Na)+.

The synthetic route of 19932-85-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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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.

Amine 2c (1 g, 3.8 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.13 g, 3.8 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lc (390 mg, 2.6 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 1 / petroleum ether 1). 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 160 mg of a white solid. Yield = 14% 1HNMR (DMSO, 200 MHz) delta 1.56 (2H, bs), 1.69 (4H, bs), 2.85 (4H, m), 4.42 (2H, d, J = 5.6 Hz), 6.66 (1H, dd, J = 8 Hz, J’ = 0.8 Hz), 7.01 (2H, m), 7.32 (1H, s), 7.44 (2H, dd, J = 7.6 Hz), 7.72 (1H, dd, J = 8.6 Hz, J’ = 1 Hz), 8.73 (1H, bs), 1 1.68 (1H, bs); [M+1] 435.2 (C2iH21F3N4O3 requires 434.4).

As the paragraph descriping shows that 81282-60-2 is playing an increasingly important role.

Reference£º
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.54903-16-1,2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 7; 4-Benzyl-piperidine-l-carboxylicacid(2-oxo-2,3-dihydro-benzooxazoIe-6-carbonyl)-amide; 7a) 2-Oxo-2,3-dihydro-benzooxazole-6-carboxylic acid amide; To a stirred solution of 0.37 g (2.06 mmol) of 2-oxo-2,3-dihydro-benzooxazole-6-carboxylic acid [EurJ.Med.Chem.Chim. Ther., 9, 491-492. (1974)], 13 ml of 1,4-dioxane and 0.1 ml of dimethylformamide 1.35 ml (18 mmol) of thionyl chloride is added droep wise below 10 C, and the reaction mixture is stirred at room temperature for 24 h. Then 10 ml of 25 % ammonium hydroxide solution is added drop wise to the mixture. The reaction mixture is concentrated and the residue is purified by column chromatography using Kieselgel 60 aes adsorbent (Merck) and Chloroform : methanol = 3:1 aes eluent to yield 0.13 g (35.3 %) of the title compound. Mp.: 296 C (2-propanol).

The synthetic route of 54903-16-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; RICHTER GEDEON VEGYESZETI GYAR RT.; WO2006/10966; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90322-32-0,2-Methylbenzo[d]oxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

N-((3R)-1-((3-(cyclopropylmethyl)-7-fluoro-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl)carbamoyl)piperidin-3-yl)-2-methyl-1,3-benzoxazole-5-carboxamide HATU (70.4 mg, 0.19 mmol) was added to a solution of (R)-3-amino-N-(3-(cyclopropylmethyl)-7-fluoro-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl)piperidine-1-carboxamide hydrochloride (70 mg, 0.15 mmol), 2-methylbenzo[d]oxazole-5-carboxylic acid (30.1 mg, 0.17 mmol) and DIEA (0.054 mL, 0.31 mmol) in DMF (2.0 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane) and crystallized from ethyl acetate/hexane to give the title compound (17.3 mg, 0.030 mmol, 19.46percent) as a white solid. 1H NMR (300 MHz, CDCl3):delta 0.28-0.48(4H,m), 1.10-1.27(1H,m), 1.50(6H,d,J=6.4 Hz), 1.52-1.67(2H,m), 1.70-1.87(1H,m), 1.88-2.04(1H,m), 2.63(3H,s), 2.83-2.99(2H,m), 3.81(2H,d,J=7.2 Hz), 3.85-4.00(2H,m), 4.02-4.15(1H,m), 4.89(1H,brs), 7.56(1H,d,J=13.2 Hz), 7.72(1H,d,J=8.3 Hz), 7.88(1H,dd,J=8.7,1.9 Hz), 8.08(1H,d,J=8.7 Hz), 8.15(1H,d,J=1.1 Hz), 8.40(1H,d,J=7.6 Hz), 8.50(1H,s).

As the paragraph descriping shows that 90322-32-0 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; ODA, Tsuneo; IMADA, Takashi; KONO, Mitsunori; SATO, Ayumu; TOMATA, Yoshihide; OCHIDA, Atsuko; ISHII, Naoki; SASAKI, Yusuke; FUKASE, Yoshiyuki; YUKAWA, Tomoya; FUKUMOTO, Shoji; (200 pag.)EP3192791; (2017); A1;,
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59-49-4, 2-Benzoxazolinone is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The step one obtained 27.2g benzooxazolone ring compound and 20ml acidic imidazole ionic liquid were added together to a 250ml neck round bottom flask and thoroughly mixed. Then the pre-mixed well 10.5ml 65% mass fraction nitric acid was added dropwise to a 250ml three-necked round bottom flask. At a temperature of 35 deg.C reacted for 2 hours. Afterwards, heating was stopped, cooled to room temperature, washed, filtration, and dried to give 6-nitrobenzooxazole 34.4g, yield was 94.4%;

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

Reference£º
Patent; Jiujiang Shanshui Technology Co., Ltd.; Feng, Yu; Ye, Youyu; Ye, Pian; (10 pag.)CN105669477; (2016); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.

General procedure: 6-bromo-3H-1,3-benzoxazol-2-one 1 (5.00 g, 23.36 mmol) wassuspended in ACN (150 mL) and K2CO3 (9.69 g, 70.09 mmol) wasadded. The reaction mixture was stirred at 80 C for 30 min. 1-(2-Chloroethyl)piperidine hydrochloride (4.30 g, 23.36 mmol) or 3-chloropropylpiperidine hydrochloride (5.5 g, 28 mmol) was addedand the reaction mixture was stirred at 80 C for another 12 h. Theinorganics were removed by filtration and the solvent was evaporated.The residue was purified by flash chromatography (DCM/MeOH(NH3), 9.8:0.2 (v/v)) to afford compounds 2 and 3.4.1.3 6-Bromo-3-[2-(piperidin-1-yl)ethyl]-1,3-benzoxazol-2-one (2) Beige solid (7.58?g, 23.1?mmol, 99%). Mp 85.1-85.8?C. 1H NMR (300?MHz, CDCl3): delta 7.36 (d, J?=?1.8?Hz, 1H), 7.31 (dd, J?=?8.3, 1.8?Hz, 1H), 6.92 (d, J?=?8.3?Hz, 1H), 3.90 (t, J?=?6.6?Hz, 2H), 2.64 (t, J?=?6.6?Hz, 2H), 2.51-2.38 (m, 4H), 1.60-1.35 (m, 6H). 13C NMR (75?MHz, CDCl3): delta 154.1, 143.1, 130.7, 126.6, 114.4, 113.5, 109.9, 56.0, 54.7, 40.3, 26.0, 24.2. LCMS m/z calc for [M+H]+: 325.1, 327.1 found: 325.1, 327.1.

19932-85-5 6-Bromobenzo[d]oxazol-2(3H)-one 29859, abenzoxazole compound, is more and more widely used in various.

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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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.

Oxalyl chloride (1.20 g, 9.4 mmol) was added dropwise to a stirred suspension of 2- mercapto-5-chlorobenzoxazol (1.28 g, 6.9 mmol) in CH2C12(37 mL) at The solution of 2,5-Dichlorobenzoxazol was added to a solution of (7-Methyl-l ,4- diazepan-l-yl)(5-methyl-2-(2H-l ,2,3-triazol-2-yl)phenyl)methanone (1.88 g, 6.3 mmol) and NEt3(3.18 g, 6.3 mmol) in DMF (24 mL) at room temperature. The reaction mixture was then stirred at 70 C for 19 hours and at 90 C for 20 hours. The reaction mixture was then cooled to room temperature and quenched with a saturated solution of NaHC03(50 mL). The organic phase was separated and washed with H20 (50 mL) followed by brine (50 mL). The organic phase was dried over MgS04, filtered and concentrated to give crude Suvorexant (3.58 g).

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

Reference£º
Patent; SANDOZ AG; BARTH, Roland; KAUFMANN, Marius; (97 pag.)WO2016/20404; (2016); A1;,
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Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5676-60-8,2-Methylbenzo[d]oxazol-6-amine,as a common compound, the synthetic route is as follows.

To a stirred solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (50 mg, 0.262 mmol), 2-methyl-l,3-benzoxazol-6-amine (47 mg, 0.314 mmol) and HATU (149 mg, 0.393 mmol) in DMF (1 mL) was added DIPEA (0.1 mL, 0.524 mmol), and the reaction mixture was stirred at room temperature for 16 hours until the reaction was complete. The suspension was diluted with H20 (3 mL), and the precipitated solid was collected by filtration, washed with minimum DCM and Et20, and dried in vacuo to provide the title compound (60 mg, 71%) as a white solid.XH NMR (400 MHz, DMSO-i/6) delta 10.36 (s, 1H), 8.66 (s, 1H), 8.31 (d, J= 2.0 Hz, 1H), 7.64 (d, J= 8.4 Hz, 1H), 7.47 (dd, J= 8.4 Hz, 2.0 Hz, 1H), 7.21 (s, 1H), 2.78 (s, 3H), 2.73 (s, 3H), 2.60 (s, 3H). ES-MS m/z: 322.0 [M+H]+. LC-MS Purity (254 nm): >99%; tR= 1.74 min.

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

Reference£º
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
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