Heterocyclic Building Blocks-Benzoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.375369-14-5,6-Bromobenzo[d]oxazole,as a common compound, the synthetic route is as follows.

Example 326; N-(5-(benzo[d]oxazol-6-yl)-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide; To a microwave vial equipped with a stirbar and charged with 6-bromobenzo[d]oxazole (0.050 g, 0.25 mmol), cesium carbonate (0.25 g, 0.76 mmol), PdCl2(dppf)*DCM (0.037 g, 0.045 mmol), N-(2-chloro-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.10 g, 0.25 mmol) in THF (3 ml) was added water (0.5 ml). The vial was capped and placed into CEM Microwave for 10 minutes at 100 C, while 100 watts of energy was supplied via Powermax (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired material in the mixture. The mixture was diluted with water and the organic layer was extracted with DCM and brine solution. The organics were collected, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was recrystallized from 5:1 DCM/MeOH and Hexanes to give N-(5- (benzo[d]oxazol-6-yl)-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (0.040 g, 39% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 404 (MH+).

375369-14-5 6-Bromobenzo[d]oxazole 17902800, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
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153403-53-3, 2-Chloro-6-fluorobenzo[d]oxazole is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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 The synthetic route of 153403-53-3 has been constantly updated, and we look forward to future research findings. Reference£º
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4570-41-6,Benzo[d]oxazol-2-amine,as a common compound, the synthetic route is as follows.

General procedure: Oxazolone (2; 0.251 mmol, 1 eq) and amine nucleophile(0.326 mmol, 1.3 eq) was dissolved in toluene (1 mL) to aconcentration of 0.251 M. The reaction mixture was stirredat 70 C for 3 h, and concentrated in vacuo. The residuewas purified by flash column chromatography on silica gelusing n-heptane/EtOAc as the eluents to afford compound.

The synthetic route of 4570-41-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Jo, Minmi; Won, Sun-Woo; Lee, Dong Guk; Yun, Jungeon; Kim, Sunhong; Kwak, Young-Shin; Archives of Pharmacal Research; vol. 41; 5; (2018); p. 481 – 489;,
Benzoxazole – Wikipedia
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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.

The product from step 2 (0.108 g, 0.6 mmol) and 2- hydroxyacetophenone (0.09 g, 0.66 mmol) were added to a round bottomed flask under nitrogen. Anhydrous pyridine (5 mL was added to it with stirring. The reaction mixture was cooled down using an ice bath. Phosphorus oxychloride (0.15 g, 0.99 mmol) was added and the reaction mixture was stirred at room temperature overnight. Pyridine was removed under vacuum and the residue was acidified with 1 N HCI (pH 4~5) and extracted with ethyl acetate. The solvent was EPO evaporated in vacuo to leave a residue which was purified by silica gel column chromatography (15 g). The eluent was a mixture of ethyl acetate and hexane in 1 :1. Fraction 1 was evaporated affording pure compound (0.0192 g, 11%).

As the paragraph descriping shows that 54903-16-1 is playing an increasingly important role.

Reference£º
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
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54903-16-1, 2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 25-mL round-bottom flask was placed 2-oxo-2,3-dihydro-1,3-benzoxazole- 6-carboxylic acid (100 mg, 0.56 mmol, 2.35 equiv), N,N-dimethylformamide (10 mL), HOBT (135 mg, 2.00 equiv) and EDCI (191 mg, 2.00 equiv). Then benzyl 4- [[(1R,3r,5S)-3-amino-8-azabicyclo[3.2.1]octane-8-sulfonyl]methyl]piperidine-1- carboxylate (100 mg, 0.24 mmol, 1.00 equiv) was added in several portions. After complete adddition, TEA (250 mg, 5.00 equiv) was added dropwise. The resulting solution was stirred for 1 h at room temperature. The mixture was concentrated under vacuumand the residue diluted with 10 mL of H2O. This mixture was extracted with 3×10 mL of ethyl acetate and the organic layers combined. The combined extracts were washed with 2×30 mL of brine, dried, and concentrated. The residue was chromatographed on a silica gel column with dichloromethane/methanol (10/1). This resulted in 100 mg (72%) of benzyl 4-[[(1R,3r,5S)-3-(2-oxo-2,3-dihydro-1,3- benzoxazole-6-amido)-8-azabicyclo[3.2.1]octane-8-sulfonyl]methyl]piperidine-1- carboxylate as yellow oil

As the paragraph descriping shows that 54903-16-1 is playing an increasingly important role.

Reference£º
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
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1750-45-4, 5-Chloro-6-hydroxybenzo[d]oxazol-2(3H)-one is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Hydroxy-5-chlorobenzo [d] oxazol-2 (3H) -one(1.8 g, 10 mmol),3-Bromomethyl-2H-1,2,3-triazole (1.8 g, 11 mmol),A mixture of potassium carbonate (2.8 g, 20 mmol) in acetonitrile (200 mL) was stirred at 70 C for 16 h,The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel eluting with petroleum ether / ethyl acetate 20: 1,To give 3 – [(2H- 1,2,3 -triazol-2-yl) methyl) -5-chloro-6- hydroxybenzo [d] oxazol-2 (3H) -one as an orange solid (2.3 g, 85%)

1750-45-4 5-Chloro-6-hydroxybenzo[d]oxazol-2(3H)-one 2734, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; Mudanjiang Medical School; Li Hailin; Wang Wei; Song Jing; Sun Zhiguo; Han Guangyu; (12 pag.)CN106928212; (2017); A;,
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Benzoxazole | C7H5NO – PubChem

54903-16-1, 2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

i. 2-oxo-2,3-dihydro-benzooxazole-6-carbonic-acid 13 (38.6 mg, 0.22 mmol), intermediate 12 (95.5 mg, 0.22 mmol) and 4-methylmorpholine (0.72 mL, 0.66 mmol) were given to DMF (3 mL). N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (41.4 mg, 0.22 mmol) and 1- hydroxybenzotriazolehydrate (29,2 mg, 0.2 mmol) were added at RT. It was stirred for 15 h at RT. The reaction mixture was poured onto water and extracted twice with ethyl acetate. The pooled organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo until dryness. The oily residue was comminuted with diethyl ether, and the emerging solid was filtered off. A colourless solid (14, 50.4 mg, 0.09 mmol, 44%) in high purity was yielded.

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

Reference£º
Patent; MERCK PATENT GMBH; SCHIEMANN, Kai; SCHULTZ, Melanie; STAEHLE, Wolfgang; WO2010/115491; (2010); A2;,
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Benzoxazole | C7H5NO – PubChem

54903-16-1, 2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a dry mixture of 27-1 (2-methoxyphenylhydrazide, 139 mg, 0.837 mmol), 27-2 (benzoxazol-2- one-6-carboxylic acid, 150 mg, 0.837 mmol), and HATU (318 mg, 0.837 mmol) was added THF (10 mL) to yield a hazy reddish solution. DIPEA (0.29 mL, 1.67 mmol) was added and the reaction was stirred at rt for 2 hr. Burgess reagent (499 mg, 2.09 mmol) was added one portion, and the reaction was heated to 60C overnight. An additional 499 mg Burgess reagent was added. and continued heating. After 4 hr, 2N KHSO4 (10 mL) was added and the resulting oily mixture was extracted 3X EtOAc. The combined organics were washed once with water, once with brine, filtered through cotton and concentrated to an orange solid which was purified by reverse phase chromatography, 20% – 60% MeCN/water/0.1% TFA to yield 67 mg 27-3(18%) MJ-T+ = 447.0. ?H NMR (400 MHz, DMSO) 8.02 – 7.97 (3H, m), 7.74 (1H, d, J=8.4 Hz), 7.64 (1H, t, J=8.2 Hz), 7.30 (1H, d, J=8.4 Hz), 7.18 (1H, t, J=7.4 Hz), 3.95 (3H, s), 3.39 (3H, s).

54903-16-1 2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid 391472, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); 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.19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.

Intermediate 4. 2- oxo-2,3-dihydro-1 ,3-benzoxazole-6-carbaldehyde To a suspension of 6-bromobenzo[d]oxazol-2(3H)-one (6.12g, 28.6mmol) in THF (60ml_) was added, at -78 C and under argon atmosphere, methylmagnesium bromide (10.6ml_ of a 3M solution in diethyl ether, 31 .8mmol) and the reaction mixture was stirred at this temperature fro 30 min. The, an additional amount of THF (240 mL) was added at a rate that the internal temperature was below -50 C. Then, tert-butyllithium (60.6ml_ of a 1.7 M solution in pentane, 103mmol) was slowly added and stirred for 45 min at -78 C. To the yellow suspension DMF (13.4ml_, 181 mmol) was then added, and the reaction mixtures was allowed to warm up to room temperature and stirring wasa continued for 3 additional hours. Water (300ml_) was then added to the crude mixture and the organic solvent was removed under reduced pressure. To the remaining aqueous phase, ethyl acetate (500ml_) and 1 N HCI (150ml_) were added and the the mixture was vigorously stirred and the organic phase was separated. The aqueous phase was further extracted with ethyl acetate (3 x 100 mL) and the combined organic extracts were washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to yield the title compound (4.75g, 96%, 94% purity by UPLC). The compound was used as this without further purification. LRMS (m/z): 162 (M-1 )-

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

Reference£º
Patent; ALMIRALL, S.A.; PUIG DURAN, Carlos; AIGUADE BOSCH, Jose; GUAL ROIG, Silvia; PRAT QUINONES, Maria; (149 pag.)WO2016/46390; (2016); 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.132244-31-6,5-Bromobenzo[d]oxazole,as a common compound, the synthetic route is as follows.

To a RBF was added at 0 C, under nitrogen, 4-(methoxycarbonyl) cyclohexanecarboxylic acid (0.484 g, 2.60 mmol), dry DCM (10 mL), dry DMF (0.040 mL, 0.520 mmol), and dropwise oxalyl chloride (0.854 mL, 5.72 mmol). The ice-bath was removed and the mixture was stirred for 45 minutes under nitrogen. The volatiles were removed on the rotovap, the crude oil diluted with dry DCM and evaporation repeated to give crude methyl 4-(chlorocarbonyl)cyclohexanecarboxylate. To a vial was added freshly synthesized methyl 4-(chlorocarbonyl)cyclohexane- carboxylate (2.60 mmol assummed), PhCl (2mL), 5-bromobenzoxazole (257 mg, 1.3 mmol) and potassium carbonate (27.6 mg, 0.200 mmol) in water (0.667 mL). The vial was sealed and the mixture stirred overnight at 140C. The mixture was cooled and volatiles were removed. The crude product was taken up in 1 : 1 ethylacetate/DCM, washed with minimal water, brine, dried over soudium sulfate, filtered, and evaporated. The crude reaction mixture was then taken up in 6 mL of acetonitrile/DMF and purified using a Shimadzu preparative HPLC employing acetonitrile/water/ammonium acetate where solvent A was 5% acetonitrile / 95% water / 10 mM ammonium acetate and solvent B was 5% water / 95% acetonitrile / 10 mM ammonium acetate with a Waters Sunfire 5mupiiota CI 8 30x100mm column at a gradient of 25-100% B and a flow rate of 40 mL/min. over 15 minutes with a 5 minute hold. Methyl 4-(5-bromobenzo[d]oxazol-2-yl)cyclohexanecarboxylate was obtained as a ~1 : 1 mixture of cis and trans isomers by NMR analysis and as a peach colored solid (100.8mgs, 23% yield). The LC/MS data was obtained on a Shimadzu analytical LCMS (ESI+) at 220nm using the following set of conditions: Waters Aquity BEH 1.7muiotaeta C18, 2.1 x 50mm column, with a gradient of 2-98%B (B = 100% HPLC grade acetonitrile/ 0.05% trifluoroacetic acid), (A = 100% HPLC grade water / 0.05% trifiuoroacetic acid), in 2 minutes with a gradient time of 1.5 minute at a flow rate of 0.8 mL/minute. LCMS Rt = 1.334 mia, m/z 337.9 & 339.9 (M + H).

132244-31-6 5-Bromobenzo[d]oxazole 21749504, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; GRANT-YOUNG, Katharine A.; SUN, Li-Qiang; LANGLEY, David R.; ST. LAURENT, Denis R.; SCOLA, Paul Michael; (126 pag.)WO2018/118848; (2018); A1;,
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