M.W:100-200 | Page 93 of 321 | Heterocyclic Building Blocks-Benzoxazole

Some tips on 2-Chloro-6-fluorobenzo[d]oxazole

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

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]+

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

Analyzing the synthesis route of 5676-60-8

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-Methylbenzo[d]oxazol-6-amine, 5676-60-8

5676-60-8, 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-Methylbenzo[d]oxazol-6-amine, cas is 5676-60-8,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4n-propylbenzenesulphonyl chloride (163 mg, 0.744 MMOL) in dichloromethane (3 mL) was added pyridine (140 uL, 1.72 MMOL) and the mixture was stirred under N2 for 5 min, after which time 6-AMINO-2-METHYLBENZOXAZOLE (105 mg, 0.709 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 pale pink solid (164 mg, 70%), single spot at Rf 0.49 (60: 40 hexane: ethyl acetate). mp 101.7-102. 3C, HPLC purity 99% (tR 2.02 min in 10% water-acetonitrile). ‘H NMR (CDCI3) : 6 7.61 (2H, m), 7.43 (1H, d, J=8.4 Hz), 7.37 (1H, d, J=1. 8 Hz), 7.19 (2H, m), 6.83 (2H, m), 2.57 (5H, m), 1.58 (2H, sextet, J=7.3 Hz), 0.88 (3H, t, J=7.3 Hz). LCMS: 329.21 (M-). FAB-MS (MH+, C17H18N203S) : calcd 331.1116, found 331.1107.

Reference：
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Application of 1,2-Thiazinane 1,1-dioxide

The chemical industry reduces the impact on the environment during synthesis,81282-60-2,7-Aminobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

81282-60-2, 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. 7-Aminobenzo[d]oxazol-2(3H)-one, cas is 81282-60-2,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of [6-(trifluoromethyl)-3-pyridyl)]-methanamine (lg, 4.7 mmol) in THF (30 mL) was added CDI (2.1 mol eq) and the mixture was heated at 70C overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (quantitative yield). The oil obtained (0.34g, 1.2 mmol) was dissolved in DMF (15 mL) and the bicyclic amine lc (Scheme 3) was added (0.8 mol eq), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (1 : 1 EtOAc:petroleum ether) to obtain the product as a white solid (0.064g, 20% Yield). ‘HNMR (DMSO, 200 MHz) delta 4.46 (d, 2H, J=6), 6.66 (d, 1H, J=8), 6.96 (t, 1H), 7.04 (bt, 1H), 7.64 (d, 1H, J=8), 7.86 (m, 2H), 8.70 (s, 1H), 8.77 (s, 1H), 1 1.60 (bs, 1H). [M+1] 358.02 (Ci5HnF3N4O3 requires 357.27).

Reference：
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Introduction of a new synthetic route about 5676-60-8

5676-60-8, 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.,5676-60-8 ,2-Methylbenzo[d]oxazol-6-amine, other downstream synthetic routes, hurry up and to see

It is a common heterocyclic compound, the benzoxazole compound, 2-Methylbenzo[d]oxazol-6-amine, cas is 5676-60-8 its synthesis route is as follows.

General procedure: To a solution of compound 3 (3.37 mmol) in DMF (10 mL), charged respective compound V (a-p) (4.04 mmol) and heated to 80 C. After3 h, TLC analysis showed complete conversion of starting materials. The reaction mixture was cooled to room temperature, charged water (30 mL) and extracted with EtOAc (2 × 20 mL). The combined organic layer was washed with water (20 mL) followed by brine and concentrated under reduced pressure to obtain gummy liquid. This crude material was triturated with MTBE to afford desired product as solid and which used as such in next step without any further purification.

Reference：
Article; Balraju, Vadla; Jogula, Sridhar; Krishna, Vagolu Siva; Meda, Nikhila; Sriram, Dharmarajan; Bioorganic Chemistry; vol. 100; (2020);,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

The important role of 41014-43-1

The chemical industry reduces the impact on the environment during synthesis,41014-43-1,2-(Chloromethyl)benzo[d]oxazole,I believe this compound will play a more active role in future production and life.

41014-43-1, 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-(Chloromethyl)benzo[d]oxazole, cas is 41014-43-1,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 2 3-[(2-Benzoxazolylmethyl)amino]-5-ethyl-6-methyl-2-(1H)-pyridinone A solution of 3-amino-5-ethyl-6-methyl-2-(1H)-pyridinone (152 mg,1.0 mmol), 2-chloromethyl-1,3-benzoxazole (1.07 mmol) and triethylamine (0.14 mL, 1.0 mmol) in acetonitrile (10 mmL) was stirred at reflux for 24 hrs. After concentrating under reduced pressure,the residue was flash chromatographed over silica gel. Elution with 5% MeOH- 95% CHCl3 gave 132 mg of product which was recrystallized from EtOH-water to give 95 mg of analytically pure product, mp 202-203C, with initial melting at 179 followed by resolidification, Anal. Calcd for C16H17N3O2:

Reference：
Patent; MERCK & CO. INC.; EP484071; (1992); A2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Downstream synthetic route of 5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one

The chemical industry reduces the impact on the environment during synthesis,3889-13-2,5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one,I believe this compound will play a more active role in future production and life.

3889-13-2, 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-Nitro-2,3-dihydro-1,3-benzoxazol-2-one, cas is 3889-13-2,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 5-Amino-3H-benzooxazol-2-one 10% Pd/C (50 mg) was added to a stirred solution of 5-nitro-3H-benzooxazol-2-one (450 mg, 2.5 mmol) in MeOH (5 mL) added under an atmosphere of hydrogen and the mixture was stirred for 3 hours. The mixture was then filtered over celite and the filtrate was evaporated to afford 380 mg (95%) of 5-amino-3H-benzooxazol-2-one. 1H NMR: (DMSO-d6): delta 6.88 (d, 1H), 6.3 (d, 1H), 6.22 (dd, 1H), 4.5 (s, 2H).

Reference：
Patent; FOREST LABORATORIES HOLDINGS LIMITED; US2009/239848; (2009); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Downstream synthetic route of 2-Methylbenzo[d]oxazol-6-amine

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%.

Reference：
Patent; Hutchison MediPharma Enterprises Limeted; US2008/255172; (2008); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Downstream synthetic route of 7-Aminobenzo[d]oxazol-2(3H)-one

81282-60-2, 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.,81282-60-2 ,7-Aminobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 7-Aminobenzo[d]oxazol-2(3H)-one, and cas is 81282-60-2, its synthesis route is as follows.

To a solution of 2-aminomethyl-5-trifluoromethylfurane (lg, 6.1 mmol) in THF (30 mL) was added CDI (2.1 mol eq) and the mixture was heated at 70C overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure(1.6g, 5.9 mmol). The oil obtained (0.3 lg, 1.19 mmol) was dissolved in DMF (20 mL) and the bicyclic amine lc (Scheme 3) was added (0.8 mol eq, 0.15g), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (100% EtOAc) to obtain the product as white solid (0.05g, 13% Yield). ‘HNMR (DMSO, 200 MHz) delta 4.37 (d, 2H, J=6), 6.48 (d, 1H, J=2), 6.70 (dd, 1H), 7.01 (m, 2H), 7.16 (m, 1H), 7.70 (dd, 1H, J=2), 8.69 (s, 1H), 1 1.62 (bs, 1H). [M+1] 341.61 (C14H10F3N3O4 requires 341.24).

The important role of 81282-60-2

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 7-Aminobenzo[d]oxazol-2(3H)-one, and cas is 81282-60-2, its synthesis route is as follows.

Amine 2b (795 mg, 3.3 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0C triphosgene (979 mg, 3.3 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lc (330 mg, 2.2 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 240 mg of a white solid. Yield = 26% ‘HNMR (DMSO, 200 MHz) delta 1.91 (4H, m), 3.22 (4H, m), 4.38 (2H, d, J = 5.4 Hz), 6.66 (1H, dd, J = 7.6 Hz, J’ = 1.2 Hz), 7.00 (3H, m), 7.19 (1H, d, J = 8 Hz), 7.39 (1H, d), 7.72 (1H, dd, J = 8.6 Hz, J’ = 1), 8.72 (1H, bs), 1 1.63 (1H, bs); [M+1] 421.3 (C2oH19F3N4O3 requires 420.4).

Share a compound : 2382-96-9

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.

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