Tag: 14441-90-8

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 50-mL round-bottom flask, was placed a solution of l-[l-[trans-3-aminocyclobu?yl]-lH-pyrazol-4-yl]ethan-l-ol (226 mg, 1.25 mmol, 1.00 eq.) in DMF (5 mL). To the solution were added 5-phenyl-l,2-oxazole-3-carboxylic acid (282 mg, 1.49 mmol, 1.00 eq.), HATU (700 mg, 1.84 mmol, 1.50 eq.) and DIEA (560 mg, 4.33 mmol, 3.00 eq.). The resulting solution was stirred for 2 hours at 25 C. The resulting solution was diluted with 100 mL of water. The resulting solution was extracted with ethyl acetate (3×50 mL) and the organic layers combined. The resulting mixture was washed with brine (2×100 mL), dried and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 1). The pure isomers were separated by Chiral- Prep-HPLC with the following conditions (Prep-HPLC-004): Column, Phenomenex Lux 5u Cellulose-4 AXIA Packed, 250*21.2mm,5um; mobile phase, Hex and IPA (hold 50.0% IPA in 15 min); Detector, UV 254/220nm. This resulted in 39.6 mg (9%) of 5-phenyl-N-[trans-3-[4- [(lR)-l-hydroxyethyl]-lH-pyrazol-l-yl]cyclobutyl]-l,2-oxazole-3-carboxamide as a white solid and 39.4 mg (9%) of 5-phenyl-N-[trans-3-[4-[(l S)-l-hydroxyethyl]-lH-pyrazol-l- yl]cyclobutyl]-l,2-oxazole-3-carboxamide as a white solid: [0299] Isomer 1: [0300] Analytical data: lH NMR (300 MHz, OMSO-d6): delta 9.31-9.28 (d, J= 7.2 Hz, 2H), 7.96-7.92 (m. 2H), 7.68 (s, 1H), 7.59-7.55 (m, 3H), 7.41 (s, 1H), 7.38 (s, 1H), 5.00-4.89 (m, 1H), 4.88-4.86 (d, J= 4.8Hz, 1H), 4.71-4.64 (m, 2H), 2.76-2.61 (m, 4H), 1.34-1.32 (d, J = 6.3 Hz, 3H). [0301] LC-MS: (M+H)+ = 353 [0302] HPLC purity: 99.24 at 254 nm [0303] Isomer 2: [0304] Analytical data: XH NMR (300 MHz, DMSO-c): delta 9.31-9.28 (d, J = 7.5 Hz, 2H), 7.96-7.93 (m, 2H), 7.68 (s, 1H), 7.57-7.55 (m, 3H), 7.41 (s, 1H), 7.38 (s, 1H), 4.97-4.89 (m, 1H), 4.88-4.86 (d, J= 4.8 Hz, 1H), 4.70-4.64 (m, 2H), 2.72-2.61 (m, 4H), 1.34-1.32 (d, J = 6.6 Hz, 3H). [0305] LC-MS: (M+H)+ = 353 [0306] HPLC purity: 99.74 at 254 nm.

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

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

into a 50-mL round-bottom flask, was placed a solution of methyl 3- aminocyclopentane-l-carboxylate (500 mg, 3.49 mmol, 1.00 eq.) in dichloromethane (10 mL). To the solution were added HATU (1.59 g, 4.18 mmol, 1.20 eq.), DIEA (1.6 g, 12.38 mmol, 3.50 eq.) and 5-phenylisoxazole-3-carboxylic acid (790 mg, 4.18 mmol, 1.20 eq.). The resulting solution was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.925 g (84%) of methyl 3-(5-phenylisoxazole-3- amido)cyclopentane-l-carboxylate as a light yellow solid. LC-MS (ES, m/z) [M+H]+ = 315.1, 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

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 containing 1.0 g (5.29 mmol) of 3-phenylisoxazole-3-carboxylic acid and 0.89 g (5.56 mmol) of tert-butyl (3-aminopropyl)carbamate in 10 mL of DMF was added 2.5 g (5.82 mmol) of COMU, followed by 2.0 mL (11.1 mmol) of DIPEA. The reaction mixture was allowed to stir at rt overnight. The solvents were removed under reduced pressure and the residue was subjected to silica gel chromatography to give 1.55 g (85%) of tert-butyl (3-(5-phenylisoxazole-3-carboxamido)propyl)carbamate as a yellow solid. LC/MS: 1.22 min, m/z=368.2 [M+K]+

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

Reference£º
Patent; Vanderbilt University; Lindsley, Craig W.; Waterson, Alex G.; Beauchamp, R. Daniel; (193 pag.)US2016/52895; (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

5-Phenylisoxazole-3-carboxylic acid (purchased from PharamCore, http://www.pharmacore.com; 100 mg, 0.50 mmol) and benzyl alcohol (79 mL, 0.75 mmol) were dissolved in 3 mL of acetonitrile and treated with EDC (144 mg, 0.75 mmol) and DMAP (184 mg, 1.51 mmol). The resulting solution was stirred for 12 h at room temperature. The reaction mixture was diluted with CH2Cl2, washed with 10% aqueous NaHCO3 solution (2x), water and 5% acetic acid solution (2x). The organic phase was collected, dried over Na2SO4, filtered and then concentrated in vacuo. Crude material obtained was recrystallized with hot acetonitrile to give 38 mg (27%) of 7 as a white solid. Mp 95-96oC; 1H NMR (300 MHz, CDCl3) 7.82 – 7.78 (2 H, m), 7.51-7.33 (8 H, m), 6.93 (1 H, s), 5.44 (2 H, s); 13C NMR (126 MHz, CDCl3) d 172.00, 160.06, 156.94, 135.07, 131.03, 129.35, 128.90, 128.88, 128.83, 126.78, 126.13, 100.18, 67.91. HRMS (EI), M+1 calcd. for C17H14NO3, 280.0968; found 280.1008. HPLC tR = 10.5 min.

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

Reference£º
Article; Moraski, Garrett C.; Markley, Lowell D.; Chang, Mayland; Cho, Sanghyun; Franzblau, Scott G.; Hwang, Chang Hwa; Boshoff, Helena; Miller, Marvin J.; Bioorganic and Medicinal Chemistry; vol. 20; 7; (2012); p. 2214 – 2220;,
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

into a 50-mL round-bottom flask, was placed a solution of 5- phenyl-1,2-oxazole-3-carboxylic acid (177.7 mg, 0.94 mmol, 1.00 eq.), 1-[1-[trans-3- aminocyclobutyl]- 1 H-pyrazol-3-yl]ethan- 1 -ol hydrochloride (246 mg, 1.13 mmol, 1.20 eq.),HATU (428.8 mg, 1.13 mmol, 1.20 eq.) and DIEA (363.9 mg, 2.82 mmol, 3.00 eq.) in DMF(10 mL). The resulting solution was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with ethyl acetate (3×20 mL) and the organic combined layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a Prep-TLC with ethylacetate/petroleum ether (2:1). This resulted in 189 mg (57%) of 5 -phenyl-N-[trans-3 -[3 -(1- hydroxyethyl)- 1 H-pyrazol- 1 -yl]cyclobutyl] -1 ,2-oxazole-3 -carboxamide as a off-white solid.

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

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 solution of 5-phenylisoxazole-3-carboxylic acid (117 mg, 0.620 mmol) in dichloromethane (2 mL) at 20 C. was added oxalyl chloride (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. The volatiles were removed in vacuo. The crude residue was dissolved in dichloromethane (2 mL) and added to a mixture of 1-((4-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-amine (0.150 g, 0.620 mmol) and triethylamine (0.188 g, 1.86 mmol) in dichloromethane (5 mL) dropwise. The reaction mixture was stirred for 0.5 h and purified by prep-HPLC (the crude sample was dissolved in N,N-dimethylformamide and loaded onto Boston C18 21¡Á250 mm 10 mum column. The mobile phases were acetonitrile/0.01% aqueous trifluoroacetic acid) to offer 5-phenyl-N-(1-((4-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-yl)isoxazole-3-carboxamide (65.5 mg, 0.158 mmol, 25%) as a white solid. 1H NMR (500 MHz, Dimethylsulfoxide-d6) delta 11.09 (s, 1H), 8.81 (d, J=5.0 Hz, 1H), 8.34 (s, 1H), 8.29 (s, 1H), 7.98 (dd, J=7.6, 1.6 Hz, 2H), 7.80 (d, J=5.0 Hz, 1H), 7.75 (s, 1H), 7.59-7.56 (m, 3H), 7.47 (s, 1H), 5.61 (s, 2H); LCMS (ESI) m/z: 414.1 [M+H]+.

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

Reference£º
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); 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.

3-aminocyclobutanecarbonitrile hydrochloride (440 mg, 4.58 mmol, 1.00 eq.), 5-phenyl-1,2-oxazole-3-carboxylic acid (866 mg, 4.58 mmol, 1.00 eq.) and HATU (2090 mg, 5.50 mmol, 1.20 eq.) in dichloromethane (18 mL) were placed in a 100-mL round-bottom flask. To the mixture was added DIEA (1773 mg, 13.72 mmol, 3.00 eq.) and the mixture was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of water. Theresulting solution was extracted with ethyl acetate and the organic layers combined. The resulting mixture was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3) to give 600 mg (49%) of N-(cis-3-cyanocyclobutyl)-5- phenylisoxazole-3-carboxamide as a white solid. LC-MS: (M+H) = 268.

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

Reference£º
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem