Category: 153403-53-3

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 2-Chloro-6-fluorobenzo[d]oxazole, and cas is 153403-53-3, its synthesis route is as follows.

Example 2 [Show Image] To N,N-dimethylformamide (10 mL) were added trans-4-amino-1-cyclohexanecarboxylic acid ethyl ester (2.08 g, 10 mmol) and triethylamine (5.0 mL, 36 mmol). The reaction solution was cooled below 5 C and stirred. To the suspension, was added N,N-dimethylformamide (4mL) solution in Compound 3A(2.23 g, 13 mmol)(EP572893) dropwise, the reaction mixture was stirred at room temperature for 2 hours. To the reaction solution, were added ethyl acetate (25 mL) and 5%-citric acid solution (25 mL). The organic layer was extracted, the water layer was repeatedly extracted with ethyl acetate (25 mL). Each of the organic layer was mixed, and the mixed organic layer was washed with 5%-brine and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure, and the residue was purified using silica gel chromatography (n-hexane – ethyl acetate 100:0?50:50(v/v)) to yield 3.04g of Compound 3B (yield 98 %) as a colorless solid. 1H-NMR (CDCl3) delta: 1.26 (t, J = 7.10 Hz, 3H), 1.27-1.38 (m, 2H), 1.58-1.68 (m, 2H), 2.04-2.13 (m, 2H), 2.23-2.34 (m, 2H), 3.63-3.79 (m, 1H), 4.14 (q, J = 7.10 Hz, 2H), 5.31 (s, 1H), 6.86-6.93 (m, 1H), 7.00 (dd, J = 8.24, 2.53 Hz, 1H), 7.23 (dd, J = 8.24, 4.82 Hz, 1H). MS: [M + H]+ m/z 307.1

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; Shionogi & Co., Ltd.; EP2505584; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

153403-53-3, 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. 2-Chloro-6-fluorobenzo[d]oxazole, cas is 153403-53-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 4-[[2-fluoro-4-(tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl]carbonyl]piperazine-l-carboxylate (1.26 g, 2.90 mmol, 1.00 equiv) in toluene (24 mL), 2-chloro-6-fluoro-l,3-benzoxazole (500 mg, 2.91 mmol, 1.00 equiv), Pd(PPh3)4 (336 mg, 0.29 mmol, 0.10 equiv), sodium carbonate (12 mL, 2M), ethanol (3.3 mL). The resulting mixture was stirred overnight at 95C. After cooling to room temperature, the resulting solution was diluted with 30 ml of water and extracted with 2×30 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with EA/DCM (3/10). This resulted in 1.1 g (86%) of the title compound as a gray solid. LC-MS (ES, m/z) 444 [M+H]+

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 2-Chloro-6-fluorobenzo[d]oxazole, 153403-53-3

Reference：
Patent; FORMA THERAPEUTICS, INC.; BAIR, Kenneth, W.; LANCIA, David, R.; LI, Hongbin; LOCH, James; LU, Wei; MARTIN, Matthew, W.; MILLAN, David, S.; SCHILLER, Shawn, E.r.; TEBBE, Mark, J.; WO2014/164749; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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.

General procedure: The mono Boc-protected diamines (1eq.) in DMF were added potassium carbonate (2eq.) and intermediates 2 or 3 (2eq). The mixture was heated at 120 oC for 2h. After cooling, the solution was taken up in ethyl acetate and washed with 1M HCl,1 M NaHCO3 and brine each for twice. The organic layer was dried and evaporated to give the crude final product. The product compound 5 was purified by silica gel column chromatography using PE-EA as an eluent.

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：
Article; Ouyang, Liang; Huang, Yuhui; Zhao, Yuwei; He, Gu; Xie, Yongmei; Liu, Jie; He, Jun; Liu, Bo; Wei, Yuquan; Bioorganic and Medicinal Chemistry Letters; vol. 22; 9; (2012); p. 3044 – 3049;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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

Example 99: N-[(/5,25)-2-[(6-Fluoro-l<3-benzoxazol-2-vl)amino1cvclopentyl1-2-(3- methyl-l,2,4-oxadiazol-5-yl)benzamide To a solution of N-[(lS,2S)-2-aminocyclopentyl]-2-(3-methyl- l,2,4-oxadiazol-5- yl)benzamide hydrochloride (Intermediate 26; 100 mg, 0.310 mmol) in dry DMSO (1 ml) was added DIPEA (162 mu, 0.929 mmol) and 2-chloro-6-fluoro-l,3-benzoxazole (CAS Number 153403-53-3; 64 mg, 0.372 mmol). The reaction was subjected to microwave irradiation at 140C for 1 hour. The reaction was then purified by reverse phase preparative HPLC (acetonitrile / water with 0.1% ammonia) to afford the title compound.1H NMR (400 MHz, DMSO-d6): delta ppm 1.55 - 1.78 (m, 4 H), 2.00 - 2.12 (m, 2 H), 2.35 (s, 3 H), 4.01 - 4.12 (m, 1 H), 4.19 - 4.29 (m, 1 H), 6.91 - 7.00 (m, 1 H), 7.15 - 7.21 (m, 1 H), 7.30 - 7.36 (m, 1 H), 7.50 - 7.56 (m, 1 H), 7.59 - 7.70 (m, 2 H), 7.89 - 7.95 (m, 1 H), 8.02 - 8.09 (m, 1 H), 8.58 - 8.65 (m, 1 H)MS ES+: 422 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; 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

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.

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, 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; 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

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.

To a solution of N-[(1S, 25)-2-arninocyclopentyl]-2-(difluoromethoxy)benzamide hydrochloride (Intermediate 11; 45 mg, 0.15 mmol) in DMSO (0.5 ml) was added DIPEA (57 mg, 0.44 mmol) and 2-chloro-6-fluoro-l,3-benzoxazole (CAS number 153403-53-3; 30 mg, 0.17 mmol). The reaction mixture was heated to 140C for 4 hours then partitioned between ethyl acetate and water. The organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (silica, 30 – 80% ethyl acetate / petrol) then purified further by reverse phase chromatography (C 8 silica, 5-95% water (with 0,05% ammonia) / (0606) acetonitrile) to afford the title compound. (0607) 3H NMR (400 MHz, DMSO- ) delta ppm 1.53 – 1 .67 (m, 2 H), 1 .67 – 1 .81 (m, 2 H), 2.01 – 2.18 (m, 2 }. 4.06 – 4.19 (m, 1 H), 4.22 – 4.32 (m, 1 H), 6.88 – 7.38 (m, 4 H), 7.52 – 7.65 (m, 1 H), 7.67 – 7.79 (m, 1 H), 8.03 – 8.17 (m, 1 H), 8.44 – 8.53 (m, 1 H), 8.77 – 8.87 (m, 1 H) (0608) MS ES+: 407

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; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; FUJIMOTO, Tatsuhiko; ROBINSON, John Stephen; WO2015/124934; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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

Amine hydrochloride (737.4 g, 2.59 mol) and 2-chloro-5-fluorobenzoxazole (457.4 g, 2.67 mol) were suspended in N,N-dimethylformamide (3.69 L). Triethylamine (2.17 L, 15.54 mol) and potassium iodide (128.9 g, 0.78 mol) were added thereto. To the mixture, 2-chloro-5-fluorobenzoxazole (457.4 g, 2.67 mol) dissolved in N,N-dimethylformamide (1.48 L) was added dropwise under ice-cooling and stirring. After finishing the drop-wise addition, the mixture was stirred under ice-cooling for 1 hour, at room temperature for 1 hour and then at 40 C. for 2 hours. The mixture was cooled to room temperature under ice-cooling. Water (5.16 L) was added dropwise and the mixture was suspended. After stirring at room temperature for 3 hours, the precipitated crystals were filtrated and washed with water (5.16 L) to give the desired crude product (903.4 g).

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; Shionogi & Co., Ltd.; US2010/273841; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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.

To a solution of N-[(/S,2S)-2-aminocyclopentyl]-3-methoxypyridine-2-carboxarnide hydrochloride (Intermediate 2; 75 mg, 0.28 mmol) and DIPEA (0.15 ml, 0.83 mmol) in DMSO (1 ml) was added 2-chloro-6-fluoro-l,3-benzoxazole (CAS number 153403-53-3; 57 mg, 0.33 mmol) and the reaction mixture was subjected to microwave irradiation at 140 C for 2 hours. The reaction mixture was partitioned between DCM and water. The organics were filtered through a hydrophobic frit and concentrated in vacuo. The crude material was purified by reverse phase preparative HPLC (eluted with acetonitrile / water containing 0.1 % ammonia) to afford the title compound. (0530) 1H NMR (DCM-ii2) delta ppm 1.66-1.82 (m, 2 H), 1.86-1.94 (m, 2 H), 2.21-2.32 (m, 1 H), 2.46-2.58 (m, 1 H), 3.91 (s, 3 H), 3.91 -3.99 (m, 1 H), 4.35-4.45 (m, 1 H), 6.55-6.66 (m, 1 H), 6.85-6.93 (m, 1 H), 6.98-7.02 (m, 1 H), 7.16-7.20 (m, 1 H), 7.45-7.56 (m, 2 H), 8.08- 8.19 (m, 1 H), 8.15-8.23 (m, 1 H) (0531) MS ES+: 371

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£º
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; FUJIMOTO, Tatsuhiko; ROBINSON, John Stephen; WO2015/124934; (2015); 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 2 [Show Image] To N,N-dimethylformamide (10 mL) were added trans-4-amino-1-cyclohexanecarboxylic acid ethyl ester (2.08 g, 10 mmol) and triethylamine (5.0 mL, 36 mmol). The reaction solution was cooled below 5 C and stirred. To the suspension, was added N,N-dimethylformamide (4mL) solution in Compound 3A(2.23 g, 13 mmol)(EP572893) dropwise, the reaction mixture was stirred at room temperature for 2 hours. To the reaction solution, were added ethyl acetate (25 mL) and 5%-citric acid solution (25 mL). The organic layer was extracted, the water layer was repeatedly extracted with ethyl acetate (25 mL). Each of the organic layer was mixed, and the mixed organic layer was washed with 5%-brine and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure, and the residue was purified using silica gel chromatography (n-hexane – ethyl acetate 100:0?50:50(v/v)) to yield 3.04g of Compound 3B (yield 98 %) as a colorless solid. 1H-NMR (CDCl3) delta: 1.26 (t, J = 7.10 Hz, 3H), 1.27-1.38 (m, 2H), 1.58-1.68 (m, 2H), 2.04-2.13 (m, 2H), 2.23-2.34 (m, 2H), 3.63-3.79 (m, 1H), 4.14 (q, J = 7.10 Hz, 2H), 5.31 (s, 1H), 6.86-6.93 (m, 1H), 7.00 (dd, J = 8.24, 2.53 Hz, 1H), 7.23 (dd, J = 8.24, 4.82 Hz, 1H). MS: [M + H]+ m/z 307.1, 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; Shionogi & Co., Ltd.; EP2505584; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem