Month: June 2021

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 2-Chloro-6-fluorobenzo[d]oxazole, and cas is 153403-53-3, its synthesis route is as follows.

Compound 6: A solution of compound 5 (4.24 g, 24.71 mmol), (+)-S-trityl-L-cysteine (8.16 g, 22.45 mmol) and DIPEA (5.6 mL, 33.67 mmol) in THF (20 mL) and methanol (35 mL) was stirred at room temperature for 24 h. Volatiles were removed in vacuo. The residue was suspended in water and acidified to pH 3 with 5% KHSO4 solution. The resulting suspension was extracted with CH2Cl2 (2*100 mL). The organic phase was washed with water, dried over Na2SO4, filtered, and the solvent removed in vacuo. The residue was purified by flash column chromatography using gradient elution from CH2Cl2/MeOH (99:1) to CH2Cl2/EtOH (9:1) to give (R)-2-(6-fluorobenzoxazol-2-ylamino)-3-tritylsulfanyl-propionic acid (7.80 g, 70%). 400 MHz 1H-NMR (DMSO-d6, ppm): 8.46 (1H, d, J=8.6 Hz) 7.40 (1H, dd, J=8.4, 2.4 Hz) 7.35-7.20 (16H, m) 6.99 (1H, ddd, J=10.2, 8.4, 2.4 Hz) 4.14-4.06 (1H, m) 2.76 (1H, dd, J=12.5, 9.6 Hz) 2.53 (1H, dd, J=12.5, 4.4 Hz). ESI-MS (m/z): 499 [M+H]+

153403-53-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,153403-53-3 ,2-Chloro-6-fluorobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; GALLEON PHARMACEUTICALS, INC.; US2011/224269; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is Benzo[d]oxazol-6-amine, and cas is 177492-52-3, its synthesis route is as follows.

Benzooxazol-6-yl- (6-bromo-imidazo[1,2-a]pyrazin-8-yl)-amine [0133] A quantity of 0.13 g (1 mmole) OF BENZOOXAZOL-6-YLAMINE is treated with 0.27 g (1 mmole) OF 6, 8-DIBROMO-IMIDAZO [1, 2-a] pyrazine in acetonitrile with 3 eq OF K2CO3 AT REFLUX FOR 16 hrs. The reaction mixture is cooled partitioned between ethyl acetate and water, the organic extracts are dried over anhydrous MgSO4 and evaporated IN VACUO to afford BENZOOXAZOL-6-YL- (6-BROMO- imidazo [1, 2-a] pyrazin-8-yl)-amine.

177492-52-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,177492-52-3 ,Benzo[d]oxazol-6-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; CELLULAR GENOMICS, INC.; WO2005/5429; (2005); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

132244-31-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Bromobenzo[d]oxazole, cas is 132244-31-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A reaction vessel was charged with acetic acid (2.016 mmol) and TBHP (70% inwater, 1.008 mmol) in acetonitrile (2 mL). After the addition of [Bpy]I (0.1008 mmol),benzoxazole (0.672 mmol) and secondary amines (1.344 mmol) were added. Then thereaction mixture was stirred at room temperature for 3.5 hours. After the reactionfinished, the mixture was extracted with dichloromethane (5 × 10 mL), and thecombined organic phases were dried over anhydrous Na2SO4. The solvent wasevaporated under vacuo, and the crude residue was purified by columnchromatography on silica gel. Aqueous phase was dried in a vacuum evaporator torecover the ionic liquid and directly reused in subsequent runs.

The chemical industry reduces the impact on the environment during synthesis,132244-31-6,5-Bromobenzo[d]oxazole,I believe this compound will play a more active role in future production and life.

Reference：
Article; Zhou, Ya; Liu, Zhiqing; Yuan, Tingting; Huang, Jianbin; Liu, Chenjiang; Molecules; vol. 22; 4; (2017);,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

22876-19-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Step 6) Synthesis of 2, 5-dichlorobenzo [d] oxazoleA mixture of 5-chlorobenzo [d] oxazole-2-thiol (3.01 g, 16.22 mmol) , sulfoxide chloride (20 mL, 272.6 mmol) and N, N-dimethylformamide (0.10 mL, 1.3 mmol) was heated to reflux and stirred for 3 hours The reaction mixture was cooled and the solvent was removed in vacuo. The resulting product was used directly in the next step.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5-Chlorobenzo[d]oxazole-2(3H)-thione, 22876-19-3

Reference：
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

59-49-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2-Benzoxazolinone, cas is 59-49-4,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

6-chloro-3-methylbenzo[d]oxazol-2(3H)-one (S8). 60% sodium hydride (1.44 g, 36 mmol) wasadded to a solution of benzoxindolidinone (3.38 g, 25 mmol) in THF (20 mL) at 0 C, and stirredat 0 C for 30 minutes. Iodomethane (2.30 mL, 37.5 mmol) was added dropwise and stirred at room temperature for 9 hours. The reaction mixture was diluted with ethanol and concentrated.The residue was diluted with water and extracted with dichloromethane. The organic layers werecombined, dried over sodium sulfate, filtered, and concentrated. The product was purified bycolumn chromatography eluting with 25% ethyl acetate/hexanes to yield S8 (1.62 g, 43%) as anoff white solid.Rf: 0.25 (25% ethyl acetate/hexanes)1H NMR (400 MHz, CDCl3): delta = 7.22 – 7.17 (m, 2H), 7.15 – 7.09 (m, 1H), 6.98 – 6.95 (m, 1H),3.41 (s, 3H)13C NMR (101 MHz, CDCl3): delta = 154.9, 142.8, 131.9, 124.0, 122.6, 110.1, 108.2, 28.2

The chemical industry reduces the impact on the environment during synthesis,59-49-4,2-Benzoxazolinone,I believe this compound will play a more active role in future production and life.

Reference：
Article; Fosu, Stacy C.; Hambira, Chido M.; Chen, Andrew D.; Fuchs, James R.; Nagib, David A.; Chem; vol. 5; 2; (2019); p. 417 – 428;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

4570-41-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Benzo[d]oxazol-2-amine, cas is 4570-41-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Step 5:To a solution of (S)-2-(4-methanesulfonyl-phenyl)-3-o-tolyl-propionic acid (214 mg, 0.67 mmol) and 2-amino-benzoxazole (90 mg, 0.67 mmol) in CH2Cl2 (10 mL) was added DMAP (24 mg, 0.2 mmol) and EDC.HCl (154 mg, 0.8 mmol).The reaction mixture was stirred at room temperature for 2 days.The reaction mixture was concentrated in vacuo.Purification by chromatography (silica, 0-1.5percent methanol/CH2Cl2 gradient), followed by RPHPLC purification (C4 reverse phase, 10-90percent acetonitrile/0.1percent aqueous TFA buffer) afforded (S)-N-Benzooxazol-2-yl-2-(4-methanesulfonyl-phenyl)-3-o-tolyl-propionamide (68 mg, 23percent): m.p. 106-108° C., LC/MS-ESI observed [M+H]+ 435, [alpha]28=+43.6° (c=0.5, methanol), 75percent ee by chiral HPLC determination.

The chemical industry reduces the impact on the environment during synthesis,4570-41-6,Benzo[d]oxazol-2-amine,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Brotherton-Pleiss, Christine E.; Walker, Keith A. M.; US2012/149718; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

4570-41-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Benzo[d]oxazol-2-amine, cas is 4570-41-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of carboxylic acid 3 in 3 mL dimethylformamide,were added trimethylamine (3 equiv), EDCI (1.2 equiv) and HOBt( 1.2 equiv) under ice-bath. After stirring at room temperature for30 min, amines (1 equiv) were added and the resulting mixture stirred for 24 h at room temperature. Reaction was detected byTLC (EtOAc/Hex 2:1). After completion of reaction, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed by brine, dried over MgSO4 and concentrated. The crude product was further purified by silica gel chromatography eluted with EtOAc/Hex 2:1 to afford pure desired compound. 4.1.3.8 N-(Benzoxazol-2-yl)-5-(4-(4-chlorophenyl)piperazin-1-yl)pentanamide (4h·HCl) The compound 4h was prepared from 3c and 2-aminobenzoxazole as a colorless solid (yield: 24.7percent). The free base was further converted into 4h·HCl as a white solid. Mp: 78-79 °C. 1H NMR (300 MHz, DMSO-d6) delta 11.19 (s, 1H), 9.80 (s, 2H), 7.59 (d, J = 7.7 Hz, 1H), 7.40 (dd, J = 7.7, 1.2 Hz, 1H), 7.36-7.19 (m, 4H), 7.01 (d, J = 9.0 Hz, 2H), 3.78 (d, J = 12.1 Hz, 2H), 3.50 (d, J = 10.9 Hz, 2H), 3.14 (m, 6H), 2.37 (t, J = 7.3 Hz, 2H), 1.75 (m, 2H), 1.63-1.47 (m, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Benzo[d]oxazol-2-amine, 4570-41-6

Reference：
Article; Cao, Yongkai; Paudel, Suresh; Zhang, Xiaowei; Kim, Kyeong-Man; Cheon, Seung Hoon; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5264 – 5272;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3 its synthesis route is as follows.

INVENTIVE EXAMPLE 1 5-Chloro-2-(4-methyl-1-piperazinyl)benzoxazole A 300 mg portion of 5-chloro-2-mercaptobenzoxazole was suspended in 50 ml of anhydrous benzene, and the suspension was mixed with 404 mg of phosphorus pentachloride and heated under reflux for 3 hours. The reaction solution was cooled in an ice bath and, with stirring, 1.6 g of 1-methylpiperazine was added thereto. After 30 minutes of stirring, the ice bath was removed to carry out 12 hours of stirring at room temperature, and then the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate and then the solvent was evaporated under a reduced pressure. Thereafter, the thus obtained mixture was purified by a silica gel column chromatography (ethyl acetate_methanol=20:1) to obtain the title compound (121 mg) in light yellow color. 1 H-NMR (CD3 OD) delta values: 2.35 (3 H, s), 2.60 (4 H, t), 3.70 (4 H, t), 7.02 (1 H, dd), 7.25 (1 H, d), 7.28 (1 H, d) MS (EI): m/z 251 (M+)

22876-19-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,22876-19-3 ,5-Chlorobenzo[d]oxazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Meiji Seika Kaisha, Ltd; Koichi Shudo; US6037342; (2000); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

72752-81-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate, cas is 72752-81-9,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of this pink solid (320 g, 1.53 mol) and K2CO3 (276 g, 2 mol) in EtOAc (3L) was added MeI (238.9g, 1.68 mol) below 20C. The mixture was stirred at room temperature for 12 hours. TLC (EtOAc/petroleum ether = 1:3) indicated the reaction was complete. Water (2L) was added to the mixture. The organic phase was separated, dried over Na2SO4 and concentrated to give 13 (320 g, 93.8%) as a pink solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate, 72752-81-9

Reference：
Article; Jonckers, Tim H.M.; Rouan, Marie-Claude; Hache, Geerwin; Schepens, Wim; Hallenberger, Sabine; Baumeister, Judith; Sasaki, Jennifer C.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 4998 – 5002;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

2382-96-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Benzo[d]oxazole-2-thiol, cas is 2382-96-9,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of thiol (1mmol) and H2O2 (37%) was stirred in solvent-free conditions at room temperature in presence of 0.006g of Fe3O4(at)L-aspartic-Gd as catalyst. Progress of the reaction was monitored by TLC. After completion, the catalyst was separated by magnetic field and crystallized to obtain pure product

The chemical industry reduces the impact on the environment during synthesis,2382-96-9,Benzo[d]oxazole-2-thiol,I believe this compound will play a more active role in future production and life.

Reference：
Article; Nemati, Mohammad; Tamoradi, Taiebeh; Veisi, Hojat; Polyhedron; vol. 167; (2019); p. 75 – 84;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem