Category: 14441-90-8

14441-90-8, 5-Phenylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

to a solution of 3-(3-[l-[(tert-butyldimethylsilyl)oxy]ethyl]-l,2,4-oxadiazol-5- yl)cyclobutan-l -amine (1.5 g, 5.04 mmol, 1.00 eq.) in dichloromethane (100 mL)was added 5- phenyl-l,2-oxazole-3-carboxylic acid (1.13 g, 5.97 mmol, 1.20 eq.), HATU (2.28 g, 6.00 mmol, 1.20 eq.) and DIEA (1.93 g, 14.93 mmol, 3.00 eq.). The resulting solution was stirred for 1 hour at room temperature. The reaction was then quenched by the addition of water and extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (l :50)to give 300 mg (13%) of 5-phenyl- N-[cw-3-(3-[l-[(tert-butyldimethylsilyl)oxy]ethyl]-l,2,4-oxadiazol-5-yl)cyclobutyl]-l,2- oxazole-3-carboxamide as a white solid. The solvent was changed to a mixture of with ethyl acetate/petroleum ether (1 :20) to give 1.4 g (59%) of 5-phenyl-N-[fra ,-3-(3-[l-[(tert- butyldimethylsilyl)oxy]ethyl]-l,2,4-oxadiazol-5-yl)cyclobutyl]-l,2-oxazole-3-carboxamide as a white solid. LC-MS: (M+H)+ = 469.

14441-90-8, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

14441-90-8, 5-Phenylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a solution of (lS)-l-[5-[(3- aminocyclobutyl)methyl]-l,3,4-thiadiazol-2-yl]ethan-l-ol hydrochloride (1.2 g, 4.80 mmol, 1.00 eq.), 5-phenyl-l,2-oxazole-3-carboxylic acid (2.36 g, 12.48 mmol, 2.60 eq.) and HCTU (6.0 g, 14.50 mmol, 3.00 eq.) in dichloromethane (50 mL) was placed in a 100-mL round- bottom flask. This was followed by the addition of DIEA (3.1 g, 23.99 mmol, 5.00 eq.) dropwise with stirring at 0C. The resulting solution was stirred for 4 hours at room temperature. The reaction was then quenched by the addition of 50 mL of water/ice and extracted with dichloromethane (3×50 mL) and the organic layers combined. The resulting mixture was washed with brine (3×30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2: 1). This resulted in 2.1 g (79%) of (lS)-l-(5-[[3-(5-phenyl-l,2- oxazole-3-amido)cyclobutyl]methyl]-l,3,4-thiadiazol-2-yl)ethyl 5-phenyl-l,2-oxazole-3- carboxylate as a off-white solid. LC-MS: (M+H)+ = 556

14441-90-8, The synthetic route of 14441-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; LEE, Po-shun; (180 pag.)WO2017/40606; (2017); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

To a stirred suspension of LAH in THF (10 mL, 1M solution in THF) at 0 C. was added a solution of 5-phenylisoxazole-3-carboxylic acid (0.9 g in 5 mL of THF) and after completion of addition the reaction was slowly warmed to room temperature (30 min). The reaction mixture was cooled to 0 C. and ethyl acetate was added (30 mL), followed by slow addition of saturated sodium sulfate solution. The solid was rinsed with ether several times and the solvent decanted. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo to get (5-phenylisoxazol-3-yl)methanol (0.8 g, 96% yield)., 14441-90-8

14441-90-8 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; VICURON PHARMACEUTICALS INC.; US2006/211603; (2006); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

14441-90-8, 5-Phenylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a solution of 5-phenyl-l,2-oxazole-3-carboxylic acid (850.5 mg, 4.50 mmol, 1.51 eq.) and 2-(3- aminocyclobutyl)ethan-l-ol hydrochloride (452 mg, 2.98 mmol, 1.00 eq.) in dichloromethane (25 mL)was placed in a 100-mL round-bottom flask. HATU (1.368 g, 3.60 mmol, 1.21 eq.) and DIEA (1.161 g, 8.98 mmol, 3.01 eq.) were added to the solution and stirred for 1 hour at room temperature. The resulting solution was diluted with 50 mL of water, extracted with chloromethane (3×30 mL) and the organic layers combined. The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN/H20=55:45 increasing to MeCN/H2O=60:40 within 2 min; Detector, UV 254 nm to give 110 mg (13%) of N-[3-(2-hydroxyethyl)cyclobutyl]-5-phenyl- l,2-oxazole-3-carboxamide as a off-white solid. The isomers were separated by Chiral-Prep- HPLC using the following conditions (Prep-HPLC-009): Column, Repaired IA, 21.2* 150mm, 5um; mobile phase, Hexane and ethanol (hold 20.0% ethanol in 20 min); Detector, UV 254/220 nm. This resulted in 23.8 mg (60%) of 5-phenyl-N-[ ram,-3-(2-hydroxyethyl)cyclobutyl]-l,2- oxazole-3-carboxamide as a white solid and 35.7 mg (70%) of 5-phenyl-N-[cw-3-(2- hydroxyethyl)cyclobutyl]-l,2-oxazole-3-carboxamide as a white solid. iV-iras-3-(2-hydroxyethyl)cyclobutyl)-5-phenylisoxazole-3-carboxamide: [0439] LC-MS: (M+H)+ = 287 [0440] Analytical data: XH NMR (CDC13, 400MHz): delta 7.83-7.81 (m, 2H), 7.54-7.49 (m, 3H), 7.05-7.02 (m, 1H), 6.97 (s, 1H), 4.72-4.67 (m, 1H), 3.73-3.68 (t, J = 10.0Hz, 2H), 2.49- 2.41 (m, 1H), 2.26-2.21 (m, 4H), 1.87-1.81 (m, 2H). [0441] HPLC purity: 99.4% at 254 nm. iV-cis-3-(2-hydroxyethyl)cyclobutyl)-5-phenylisoxazole-3-carboxamide: [0442] LC-MS: (M+H)+ = 287 [0443] Analytical data: XH NMR (CDC13, 400MHz): 7.83-7.80 (m, 2H), 7.54-7.49 (m, 3H), 7.02-6.93 (m, 3H), 4.50-4.44 (m, 1H), 3.67-3.63 (t, J= 8.0Hz, 2H), 2.68-2.62 (m, 2H), 2.22- 2.13 (m, 1H), 1.76-1.66 (m, 4H). [0444] HPLC purity: 99.0% at 254 nm., 14441-90-8

The synthetic route of 14441-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Into a 100-mL round-bottom flask, was placed a solution of [ -trans-3- aminocyclobutyl]-lH-pyrazol-3-yl]methanol (120 mg, 0.72 mmol, 1.00 eq., prepared using similar procedure as shown in example 29) in dichloromethane (5 mL). To the solution were added 5-phenyl-l ,2-oxazole-3-carboxylic acid (163 mg, 0.86 mmol, 1.20 eq.) and HCTU (360 mg, 0.87 mmol, 1.20 eq.). This was followed by the addition of DIEA (278 mg, 2.15 mmol, 3.00 eq.) dropwise with stirring. The resulting solution was stirred for 1 hour at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with dichloromethane (3×50 mL). The organic layers were combined, dried and concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (Waters): Column, Bridget Prep C18 5um OBDTM 19* 100mm; mobile phase, water with 0.05% NH4HCO3 and CH3CN (40.0% CH3CN up to 80.0% in 10 min, up to 95.0% in 1.5min, down to 40.0% in 1.5min); Detector, 254nm. This resulted in 44.7 mg (18%) of 5- phenyl-N-frara-S-fS-^ydroxymethy^-lH-pyrazol-l-ylJcyclobutylJ-l^-oxazole-S-carboxamide as a white solid. [0382] LC-MS: (M+H)+ = 339 [0383] Analytical data: lH NMR (400MHz, DMSO-i): delta 9.32-9.30 (d, J= 6.8 Hz, 1H), 7.95-7.94 (d, J = 6.0 Hz, 2H), 7.74 (s, 1H), 7.57-7.55 (m, 3H), 7.38 (s, 1H), 6.20 (s, 1H), 5.02- 4.99 (t, J= 5.6Hz, 1H), 4.96-4.95 (m, 1H), 4.71-4.65 (m, 1H), 4.44-4.42 (d, J= 6.0 Hz, 2H), 2.75-2.63 (m, 4H). [0384] HPLC purity: 98.8% at 254 nm., 14441-90-8

The synthetic route of 14441-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Step 1: ethyl 5-(2-(5-phenylisoxazole-3-carboxamido)ethyl)-1,3,4-thiadiazole-2-carboxylate HATU (0.45 g, 0.001 mol) was added to a solution of 5-phenylisoxazole-3-carboxylic acid (0.15 g, 0.7 mmol) and ethyl 5-(2-aminoethyl)-1,3,4-thiadiazole-2-carboxylate (0.2 g, 1 mmol) in THF (4 mL) followed by DIPEA (0.3 g, 2 mmol) and the resulting reaction mixture was stirred at room temperature for 4 h. Progress of the reaction was monitored by TLC. The reaction mixture was poured onto ice cooled water (10 mL) and the precipitate thus formed was filtered. Residue was washed with water and hexane (2*10 mL) and dried under reduced pressure to afford the product (0.14 g, 48.2%) as off white solid. 1H NMR (400 MHz, CDCl3): delta 7.79-7.76 (m, 2H), 7.50-7.45 (m, 3H), 7.38 (t, J=5.6 Hz, 1H), 6.93 (s, 1H), 4.50 (q, J=7.1 Hz, 2H), 4.00 (q, J=6.3 Hz, 2H), 3.51 (t, J=6.4 Hz, 2H), 1.44 (t, J=7.1 Hz, 3H); LC-MS: [M+H]+=373.7.

14441-90-8, 14441-90-8 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; PROTEOSTASIS TEHRAPEUTICS, INC.; Bastos, Cecilia M.; Munoz, Benito; Tait, Bradley; (48 pag.)US2017/1993; (2017); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Thionyl chloride (1.2 mL) was added at 0 C to the 3-phenylisoxazole-5-carboxylic acid 13 or the 5-phenylisoxazole-3-carboxylic acid 14 or the 5-(4-chlorophenyl)isoxazole-3-carboxylic acid 15 or the 3-(4-methylphenyl)isoxazole-5-carboxylic acid 16 (0.3 g, 1.58 mmol). The obtained suspension was stirred and heated at reflux for 16 h and then cooled at 0 C. At this temperature, a new addition of thionyl chloride (1.2 mL) was followed by another heating at reflux for 2 h. The reaction mixture was cooled at room temperature and the thionyl chloride excess was evaporated to dryness in vacuo. Anhydrous THF (2 mL) was added to the crude product. To the resulting solution, cooled at -5 C, was added dropwise a solution of appropriate amine (3.16 mmol) in dry THF (2 mL). The reaction mixture was stirred at room temperature for ca. 90 min (TLC, petroleum ether/ethyl acetate) and then the solid mass was filtered off and washed with THF. The filtrate was evaporated to dryness; the residue was treated with saturated sodium bicarbonate solution (20 mL) and extracted with dichloromethane (3¡Á15 mL). The combined organic phases were dried (Na2SO4) and evaporated to dryness to give the crude product, purified by flash-chromatography to give the desired amide.

14441-90-8, 14441-90-8 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Cosimelli, Barbara; Simorini, Francesca; Taliani, Sabrina; La Motta, Concettina; Da Settimo, Federico; Severi, Elda; Greco, Giovanni; Novellino, Ettore; Costa, Barbara; Da Pozzo, Eleonora; Bendinelli, Sara; Martini, Claudia; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4506 – 4520;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a solution of carboxylic acid 21-29 (1 equiv) in anhydrous CH2Cl2 were successively added HBTU (1.5 equiv), HOBt (0.5 equiv) and DIPEA (2 equiv). The mixture was stirred for 45 min at room temperature. Then, the appropriate amine (1.1 equiv) was introduced and the stirring was continued for 24 h. At the end of the reaction, the mixture was filtered off and the filtrate was successively washed with saturated aqueous NaHCO3 solution, 1N aqueous HCl and distilled water. The organic layer was dried over MgSO4 and was concentrated in vacuo. The resulting residue was purified by TLC (cyclohexane/AcOEt, 7:3) and crystallized in absolute EtOH to give carboxamide 30-48.

14441-90-8, The synthetic route of 14441-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Andrzejak, Virginie; Muccioli, Giulio G.; Body-Malapel, Mathilde; El Bakali, Jamal; Djouina, Madjid; Renault, Nicolas; Chavatte, Philippe; Desreumaux, Pierre; Lambert, Didier M.; Millet, Regis; Bioorganic and Medicinal Chemistry; vol. 19; 12; (2011); p. 3777 – 3786;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

a solution of [5-[(3-aminocyclobutyl)methyl]-l,3,4-thiadiazol-2-yl]methanol hydrochloride (500 mg, 2.12 mmol, 1.00 eq., 99%), 5-phenyl-l,2-oxazole-3-carboxylic acid (481 mg, 2.54 mmol, 1.20 eq.), HCTU (1.061 g, 2.55 mmol, 1.20 eq.) and DIEA (1.09 g, 8.43 mmol, 1.20 eq.) in dichloromethane (30 mL) was stirred for 2 hours at room temperature. The resulting mixture was concentrated under vacuum. The crude product was purified by Prep- Flash with acetonitrile and water (0-46% within 40 min). The isomers were separated by Prep- SFC with the following conditions (prep SFC 350-2): Column, Phenomenex Lux 5mu Cellulose- 4, 250*50mm; mobile phase, C02 (50%), MeOH (0.2%DEA) (50%); Detector, UV 220nm. 5-phenyl-iV- [(cis-3- [ [5-(hydroxymethyl)-l,3,4-thiadiazol-2-yl] methyl] cyclobutyl] – 1,2- oxazole-3-carboxamide: [0157] Yield: 37% [0158] Appearance: off-white solid [0159] Analytical data: XH NMR (400MHz, OMSO-d6, ppm): delta: 9.06 (d, J= 8.0Hz, 1H), 7.94-7.92 (m, 2H), 7.58-7.54 (m, 3H), 7.35 (s, 1H), 6.14-6.11 (m, 1H), 4.80 (d, J= 6.0Hz, 2H), 4.35-4.33 (m, 1H), 3.19-3.17 (m, 2H), 2.43-2.33 (m, 3H), 1.99-1.93 (m, 2H). [0160] LC-MS: 371.1 [M+H]+ 5-phenyl-iV- [(trans-3- [ [5-(hydroxymethyl)-l,3,4-thiadiazol-2-yl] methyl] cyclobutyl] – 1,2- oxazole-3-carboxamide: [0161] Yield: 37% [0162] Appearance: light yellow solid [0163] Analytical data: NMR (400MHz, OMSO-d6, ppm): delta: 9.14 (d, J= 7.2Hz, 1H), 7.94-7.92 (m, 2H), 7.56-7.54 (m, 3H), 7.36 (s, 1H), 6.14-6.11 (m, 1H), 4.80 (d, J= 6.0Hz, 2H), 4.63-4.55 (m, 1H), 3.33-3.28 (m, 2H), 2.51-2.49 (m, 1H), 2.33-2.31 (m, 2H) , 2.14-2.13 (m, 2H).

14441-90-8, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; LEE, Po-shun; (180 pag.)WO2017/40606; (2017); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem