Day: June 1, 2021

As a common heterocyclic compound, it belongs to benzoxazole compound, name is Benzo[d]oxazol-2-amine, and cas is 4570-41-6, its synthesis route is as follows.

Example I (0279) (0280) I (0281) 2-Bromopyridine (1 ) (1.0g, 6.3mmol), benzo[d]oxazol-2-amine (2) (0.871 g, 6.4mmol), Xantphos (0.37g, 0.63mmol) and Cs2C03 (3.09g, 9.4mmol) were combined in dry 1 ,4-dioxane (15mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10min. Pd2(dba)3 (0.289g, 0.31 mmol) was then added and the resulting reaction mixture was heated at 90°C for 30h. It was then poured onto demineralised water (200ml_) and extracted with EtOAc (3 x 100ml_). The organic phases were combined, dried over Na2S04, filtered and subsequently concentrated in vacuo. The resulting residue was purified by flash chromatography with EtOAc/Hexane (1 : 1) to provide N-(pyridin-2-yl)benzo[d]oxazol-2-amine (3) as a yellow solid (0.8g, 60percent). (0282) LCMS (ES): Found 212.1 [M+H]+.

4570-41-6, 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.,4570-41-6 ,Benzo[d]oxazol-2-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; WHALE, Andrew David; COLMAN, Lucy Mary; ROGERS, Helen Louise; (117 pag.)WO2017/208032; (2017); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, Benzo[d]oxazol-2-amine, cas is 4570-41-6 its synthesis route is as follows.

[000213] To a stirred solution of crude acid chloride (70 mg, crude) in CH2C12 (5 mL) under argon atmosphere were added 2-chloro-4-fluoroaniline 184 (25 mg, 0.17 mmol) and pyridine (0.07 mL, 0.86 mmol) at 0 °C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with CH2C12 (2 x 30 mL). The combined organic extracts were washed with 1 N HC1 (20 mL), 10percent NaHCO3 solution (30 mL), brine (15 mL) dried over sodium sulfate, filtered and concentrated in vacuo to obtain crude. The precipitated material was either directly dried in vacuo or triturated or purified through silica gel column chromatography /preparative HPLC or by acid-base treatment to afford the desired compound.

4570-41-6, 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.,4570-41-6 ,Benzo[d]oxazol-2-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 4-Aminobenzo[d]oxazol-2(3H)-one, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 81900-93-8, its synthesis route is as follows.

Amine 2b (289 mg, 1.2 mmol) (Scheme 7) was dissolved in 20ml of AcOEt and at 0C triphosgene (356 mg, 1.2 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 lb (180 mg, 1.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). 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 lOOmg of a white solid. Yield = 20% ‘HNMR (DMSO, 200 MHz) delta 1.94 (4H, m), 3.23 (4H, m), 4.67 (2H, d, J = 5.6 Hz), 6.55 (2H, dd, J = 8.8 Hz, J’ = 1.2 Hz), 7.05 (1H, t, J = 8.2 Hz), 7.17 (2H, d, J = 7.2 Hz), 7.46 (1H, d), 9.98 (1H, t), 1 1.53 (1H, bs), 1 1.80 (1H, bs); [M+1] 421.2 (C2oH19F3N4O3 requires 420.39).

81900-93-8, 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.,81900-93-8 ,4-Aminobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

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

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 2-Methylbenzo[d]oxazol-6-amine, and 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.

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

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

151230-42-1, 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. 6-Bromo-2-methylbenzo[d]oxazole, cas is 151230-42-1,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of Compound 24 (480 mg, 2.264 mmol) in 1,4-dioxane (7 mL) were added TETRAKIS(TRIPHENYLPHOSPHINE) PALLADIUM (0) (183 mg, 0.158 mmol), PHENYLBORONIC ACID (414 mg, 3.40 mmol) and 2M aqueous potassium phosphate solution (3.4 ml, 6.8 mmol) under nitrogen atmosphere at room temperature, then the reaction mixture was stirred at 150 C. for 40 minutes under microwave irradiation. To the reaction solution was added 1N hydrochloric acid, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound 25 (385 mg, 81%).Compound 25; 1H-NMR (DMSO-d6) delta: 2.64 (s, 3H), 7.38 (dd, J=8.4, 2.0 Hz, 1H), 7.47-7.51 (m, 2H), 7.64 (d, J=2.0 Hz, 1H), 7.77-7.75 (m, 3H), 7.96 (s, 1H)

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 6-Bromo-2-methylbenzo[d]oxazole, 151230-42-1

Reference：
Patent; Shionogi & Co., Ltd.; US2012/253040; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

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 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

Reference：
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

864274-04-4, 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-Methylbenzo[d]oxazole-6-carbaldehyde, cas is 864274-04-4,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To the solution of 2-(2,6 dichloro-phenylimino)-thiazolidin-4-one (483 mg, 1.85 mmol) in acetic acid (8 mL) was added 2-methyl-benzooxazole-6-carbaldehyde (300 mg, 1.85 mmol, 1 eq) followed by sodium acetate (0.8 g). The reaction mixture was refluxed for 48 hours and water (10 mL) was added. Solid was filtered and purified by column chromatography (1 :5 ethyl acetate:dichloromethane) to give 1 10 mg (15 percent yield) of pure 2-(2,6-dichloro-phenylimino)-5-(2-methyl-benzooxazol-6-yl- methylene)-thiazolidin-4-one. 1H-NMR (CDCI3): D2.69 (s, 3H), 7.12 (t, 1 H, J=8.1 Hz), 7.36 (d, 3H, J=7.8 Hz), 7.56 (s, 1 H), 7.70 (d, 1 H, J=8.1 Hz), 7.88 (s, 1 H), 9.69 (s, 1 H). LC MS (m/e) = 404.0 (MH+). Rt = 2.36 min.

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]oxazole-6-carbaldehyde, 864274-04-4

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/103755; (2007); A2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 5-Bromobenzo[d]oxazole, cas is 132244-31-6 its synthesis route is as follows.

To a solution of 5-bromobenzo[d]oxazole (1.2 g, 6.06 mmol, 1 eq.) in DMF (10 mL) was added 5-(4,4,5,5-Bis(pinacolato)diboron (1.68 g, 1.66 mmol, 1.1 eq.), KOAc (1.7 g, 18.09 mmol, 3 eq.), and PdCl2(dppf)?DCM complex (247 mg, 0.23 mmol, 0.05 eq.). The reaction mixture was deoxygenated with N2 and the reaction mixture was stirred at 80 C. for 18 h. The progress of the reaction was monitored by LCMS The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with ethyl acetate (2*50 mL). Combined organic layer was washed with brine (20 mL) and dried over sodium sulfate. Removal of solvent under reduced pressure gave crude which was purified by flash chromatography(0-100% Hexane-EtOAc) to afford 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (0.900 g, 60%) as off white solid. LCMS: 245, 247 [M+1]+

132244-31-6, 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.,132244-31-6 ,5-Bromobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (120 pag.)US2019/23666; (2019); 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 4-chloro-6-methylpyrimidin-2-amine (1)(1 mmol) in dry ethanol (4 ml), benzoxazol-2-amine (2a)/benzothiazol-2-amine (2b)/1H-benzimidazol-2-amine (2c)(1.1 mmol) and a catalytic amount of methanesulfonic acid(0.2 ml) were added and refluxed for 5?7 h. After completionof the reaction the contents were cooled and dilutedwith water (15 ml). The separated solid was filtered, washedwith water, dried and recrystallized from 2-propanol. N4-(1,3-Benzoxazol-2-yl)-6-methyl-2,4-pyrimidinediamine(4a)Red solid; yield 74percent; m.p. 138?140 °C; IR (KBr) vmax 3478(NH2), 3381, 3320 (NH), 1578 (C=N) cm?1; 1H NMR(DMSO?d6, 400 MHz): delta = 2.47 (s, 3H, CH3), 7.01 (s, 1H,C5?H), 7.12 (s, 2H, NH2), 7.33?7.49 (m, 4H, Ar?H), 8.27(bs, 1H, NH); 13C NMR (DMSO?d6, 100 MHz): delta = 24.9(CH3), 96.1 (C?5), 160.4 (C?2?), 164.4 (C?2), 167.5 (C?6),171.9 (C?4), 112.3, 121.6, 125.9, 126.7, 143.4, 152.5(aromatic carbons); MS (m/z): 241.25 [M+]. Anal. Calcd.for C12H11N5O: C, 59.74; H, 4.60; N, 29.03. Found: C,59.86; H, 4.62; N; 29.24.

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 4570-41-6, Benzo[d]oxazol-2-amine

Reference：
Article; Seenaiah, Dandu; Rekha, Tamatam; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 2; (2017); p. 431 – 441;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 5-Chlorobenzo[d]oxazole-2(3H)-thione, and cas is 22876-19-3, its synthesis route is as follows.

Thiol 9a (10.5 kg, 54.6 mol) was added to a vessel and suspended in DCM (141 kg). Oxalyl chloride (10.4 kg, 82.3 mol) was added (slightly endothermic) followed by DMF (40.0 kg, 547 mol) over 1.25 h, such that the batch temperature was 25 C. The batch was aged at 20 C. forapproximately 30 mi HPLC analysis showed reaction to becomplete. The batch was cooled to 10 C. then triethylamine (16.64 kg, 164.4 mol) was added via a sub-surface sampleline at such a rate as to maintain a batch temperature of 10C. A sub-surface addition protocol was required to preventbuild up of triethylamine hydrochloride solid on the walls ofthe vessel. The batch was cooled to 00 C., then a solution ofN-l3oc-ethylenediamine (10.5 kg, 61.2 mol)inDCM(lOkg)was added such that the batch temperature was 10 C. Thereaction was warmed to 20 C. and stirred for 2.5 h, HPLCanalysis showed the reaction to be complete. Water (63.6 kg)was charged to the batch and the mixture stirred for 5 mm.The layers were separated and the aqueous phase re-extracted with DCM (42.2 kg). The organic solutions werethen combined and approximately half of the total DCMvolume was distilled from the batch under vacuum whilstmaintaining a temperature of 40 C. MeCN (83.3 kg) wasthen added and the remaining DCM removed by distillation(0.5 mol % DCM left by ?H NMR wrt MeCN). MVK (4.61kg, 65.8 mol) was added to the batch followed by DI3U (4.17kg, 27.4 mol) such that the temperature was 20 C. Thebatch was aged for 10 h at 20 C. then analyzed by HPLC.The reaction was then diluted with water (42.4 kg) and agedfor a further 30 mm. The mixture was filtered and the slurrywashed with MeCN (33.3 kg). The solid was washed withMeCN (.-10 L) then dried in a vacuum oven (T=60 C.) for22 h. MVK adduct 10 (15.5 kg) was isolated as an off-whitesolid. mp 145-148 C. ?H NMR (400 MHz, CDC13): oe 7.24(d, 1H, J=2.3 Hz), 7.09 (d, 1H, J=8.5 Hz), 6.91 (dd, 1H,J=8.5, 2.3 Hz), 5.06 (s, 1H, br), 3.73 (t, 2H, J=6.7 Hz), 3.63(t, 2H, J=6.1 Hz), 3.37 (d, 2H, br), 2.89 (t, 2H, J=6.7 Hz),2.14 (s, 3H), 1.33 (s, 9H). ?3C NMR (100.6 MHz, CDC13):206.7, 163.0, 156.0, 147.4, 144.6, 129.2, 120.3, 116.6,109.2, 79.4, 49.3, 44.3, 41.9, 39.1, 30.2, 28.3. HRMS (ESI):mlz [M+H] calcd for C,8H24C1N304: 382.1534; found:

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; MERCK SHARP & DOHME CORP.; Fleitz, Fred; Mangion, Ian; Yin, Jingjun; (11 pag.)US9441254; (2016); B2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem