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

Example 9; 1 -(4-(5-(4-( 1 , 1 -Difluoroethyl)-5-phenylisoxazol-3 -yl)- 1 ,2,4-oxadiazol-3 – yl)benzyl)azetidine-3-carboxylic acid, 2,2,2-trifluoroacetic acid salt; 9-A. Methyl S-phenylisoxazole-S-carboxylate; [00179] A solution of S-phenylisoxazole-S-carboxylic acid (0.86 g, 4.55 mmol) in toluene (15.0 mL) and methanol (3 mL) was added a 2M solution of TMS- diazomethane in hexanes (3.1 mL, 6.14 mmol) dropwise at room temperature. The reaction mixture was stirred for 30 minutes and concentrated. The residue was dispersed in methanol (3 mL), stirred for 5 minutes, and filtered to give methyl 5- phenylisoxazole-3-carboxylate (897 mg). The compound had an HPLC ret. time = 2.67 min. : YMC S5 COMBISCREEN 4.6X50 mm; Gradient time: 4 min; Flow rate = 4 ml/min; Solvent A = 10% MeOH – 90% Water – 0.2% H3PO4; Solvent B = 90% MeOH – 10% water – 0.2% H3PO4; Start % B = O; Final % B = 100. LC-MS: M+1 = 204+., 14441-90-8

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott, Hunter; DYCKMAN, Alaric, J.; PITTS, William, J.; SPERGEL, Steven, H.; WO2010/85581; (2010); 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.

a solution of [5-[3- (aminomethyl)cyclobutyl]-l,3,4-thiadiazol-2-yl]methanol hydrogen chloride (750 mg, 3.17 mmol, 1.00 eq.), 5-phenyl-l,2-oxazole-3-carboxylic acid (860 mg, 4.55 mmol, 1.40 eq.), HCTU (1.59 g, 3.82 mmol, 1.20 eq.) and DIEA (1.66 g, 12.84 mmol, 3.00 eq.) in dichloromethane (50 mL) was stirred for 3 hours at 25 C. The resulting mixture was concentrated under vacuum. This resulted in 800 mg (crude) [5-(3-[[(5-phenyl-l,2-oxazol-3- yl)formamido]methyl]cyclobutyl)-l,3,4-thiadiazol-2-yl]methyl 5-phenyl-l,2-oxazole-3- carboxylate as a yellow oil. The crude product was used in the next step directly without further purification. LC-MS: 542.0 [M+H]+.

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

14441-90-8, Example 9; 1 -(4-(5-(4-( 1 , 1 -Difluoroethyl)-5-phenylisoxazol-3 -yl)- 1 ,2,4-oxadiazol-3 – yl)benzyl)azetidine-3-carboxylic acid, 2,2,2-trifluoroacetic acid salt; 9-A. Methyl S-phenylisoxazole-S-carboxylate; [00179] A solution of S-phenylisoxazole-S-carboxylic acid (0.86 g, 4.55 mmol) in toluene (15.0 mL) and methanol (3 mL) was added a 2M solution of TMS- diazomethane in hexanes (3.1 mL, 6.14 mmol) dropwise at room temperature. The reaction mixture was stirred for 30 minutes and concentrated. The residue was dispersed in methanol (3 mL), stirred for 5 minutes, and filtered to give methyl 5- phenylisoxazole-3-carboxylate (897 mg). The compound had an HPLC ret. time = 2.67 min. : YMC S5 COMBISCREEN 4.6X50 mm; Gradient time: 4 min; Flow rate = 4 ml/min; Solvent A = 10% MeOH – 90% Water – 0.2% H3PO4; Solvent B = 90% MeOH – 10% water – 0.2% H3PO4; Start % B = O; Final % B = 100. LC-MS: M+1 = 204+.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott, Hunter; DYCKMAN, Alaric, J.; PITTS, William, J.; SPERGEL, Steven, H.; WO2010/85581; (2010); 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

DIEA (943 mg, 7.30 mmol, 3.00 eq.) was added dropwise to a cold solution of 5-phenylisoxazole-3-carboxylic acid (550 mg, 2.91 mmol, 1.20 eq.), trans-3 -[5- [(1 R)- 1 -methoxyethyl] -1,3 ,4-oxadiazol-2-yl]cyclobutan- 1-amine (480 mg, 2.43mmol, 1.00 eq.) and HATU (1.387 g, 3.65 mmol, 1.50 eq.) in dichloromethane (50 mL) at 0 C. The resulting solution was stirred for 1 hour at room temperature and then diluted with 50 mL of dichloromethane. The resulting mixture was washed with water (2×50 mL) and brine (1×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to give 628 mg (70%)of 5 -phenyl-N- [trans-3 -[5- [(1 R)- 1 -methoxyethyl]- 1,3 ,4-oxadiazol-2-yl]cyclobutyl] isoxazole-3 – carboxamide as an off-white solid.[0535] Analytical data:[0536] HPLC purity: 98.9% at 254 nm[0537] LC-MS (ES, m/z): [M+1] = 369[0538] ?H NMR (400MHz, DM50-cl6): 9.33-9.31 (d, J= 7.6 Hz, 1H), 7.96-7.94 (t, J= 5.6Hz, 2H), 7.59-7.56 (m, 3H), 7.38 (s, 1H), 4.74-4.67 (m, 2H), 3.76-3.70 (m, 1H),3.29 (s, 3H), 2.74-2.61 (m, 4H), 1.5 1-1.49 (d, J= 6.8 Hz, 3H)., 14441-90-8

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

Reference£º
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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

Step-4: N-(2-(5-(methoxymethyl)-1,3,4-thiadiazol-2-yl)ethyl)-5-phenylisoxazole-3-carboxamide To an ice-cooled suspension of 5-phenyl-isoxazole-3-carboxylic acid (2.08 g, 0.011 mol) in DCM (40 mL) was slowly added T3P solution (10.5 mL, 0.016 mol, 50% solution in EtOAc) followed by addition of triethylamine (2.23 g, 0.022 mol) and solution of 2-(5-methoxymethyl-[1,3,4]thiadiazol-2-yl)-ethylamine (1.88 g, ca. 0.011 mol) in DCM (10 mL). The reaction mixture was stirred at room temperature for 18 h and quenched onto ice-water (150 mL). Separated DCM layer was washed with saturated NaHCO3 solution (3*75 mL), water (2*50 mL) and brine (100 mL). Organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to obtained crude solid product. The crude solid was triturated in diethyl ether (50 mL), filtered and dried to afford desired product. Yield: 48%; Appearance: off-whites solid Analytical data: 1H NMR (400 MHz, CDCl3): delta 7.79-7.76 (m, 2H), 7.50-7.46 (m, 3H), 7.41 (br, 1H), 6.93 (s, 1H), 4.82 (s, 2H), 3.99-3.94 (m, 2H), 3.45 (s, 3H), 3.42-3.41 (m, 2H). LC-MS: (M+H)+ 345.0; HPLC Purity: 99.87% at 254 nm & 99.32% at 220 nm.

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

Reference£º
Patent; PROTEOSTASIS TEHRAPEUTICS, INC.; Bastos, Cecilia M.; Munoz, Benito; Tait, Bradley; (48 pag.)US2017/1993; (2017); 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

14441-90-8, 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- [(ci’s-3- [ [5-(hydroxymethyl)-l,3,4-thiadiazol-2-yl] methyl] cyclobutyl] – 1,2- oxazole-3-carboxamide: [0198] Yield: 37% [0199] Appearance: off-white solid [0200] 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). [0201] 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: [0202] Yield: 37% [0203] Appearance: light yellow solid [0204] 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 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various fields.

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.

Et3N (5.6 mL, 42 mmol) and HATU (4.84 g, 13 mmol) were added to a mixture of ethyl trans-3-aminocyclobutane-1-carboxylate hydrochloride (1.89 g, 10 mmcl) and 5-phenyliscxazcle-3-carbcxylic acid (2 g, 10 mmcl) in THF (200 mL) at room temperature and the reaction mixture was stirred for 6 h at room temperature. Volatiles were removed under reduced pressure to get the crude compound. The reaction mixture was diluted with water (100 mL) and extracted using ethyl acetate (2 x 75 mL). Combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Themixture was purified by flash column chromatography using 30% EtOAc in hexane as eluent to give the product (2.65 g, 80 %) as white solid. ?H NMR (400 MHz, CDC13) : oe 7.80-7.77 (m, 2H), 7.49-7.46 (m, 3H), 7.00 (d, J= 7.2 Hz, 1H), 6.94 (s, 1H), 4.79-4.73 (m, 1H), 4.17 (q, J=7.1 Hz, 2H), 3.10-3.09 (m, 1H), 2.78-2.72 (m, 2H), 2.40-2.32 (m, 2H), 1.30-1.26 (t, J 7.2 Hz, 3H). LC-MS: [M+H] + 315.2

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; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

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

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

Epsilon Nu (5.6 mL, 42 mmol) and HATU (4.84 g, 13 mmol) were added to a mixture of ethyl fras-3-aminocyclobutane-l-carboxylate hydrochloride (1.89 g, 10 mmol) and 5- phenylisoxazole-3-carboxylic acid (2 g, 10 mmol) in THF (200 mL) at room temperature and the reaction mixture was stirred for 6 h at room temperature. Volatiles were removed under reduced pressure to get the crude compound. The reaction mixture was diluted with water (100 mL) and extracted using ethyl acetate (2 x 75 mL). Combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The mixture was purified by flash column chromatography using 30% EtOAc in hexane as eluent to give the product (2.65 g, 80 %) as white solid. Ti NMR (400 MHz, CDC13) : delta 7.80-7.77 (m, 2H), 7.49-7.46 (m, 3H), 7.00 (d, J = 7.2 Hz, 1H), 6.94 (s, 1H), 4.79-4.73 (m, 1H), 4.17 (q, J = 7.1 Hz, 2H), 3.10-3.09 (m, 1H), 2.78-2.72 (m, 2H), 2.40-2.32 (m, 2H), 1.30-1.26 (t, J= 7.2 Hz, 3H). LC-MS: [M+H] + 315.2

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

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