Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62348-13-4,Isoxazole-5-carbonyl chloride,as a common compound, the synthetic route is as follows.

62348-13-4, EXAMPLE 11 Preparation of 5-chloro-2-(isoxazol-5-yl)-7-[2-(pyridin-2-yl)ethyl]-benzoxazole This is prepared from 2-amino-4-chloro-6-[2-(pyridin-2-yl)ethyl]phenol and isoxazole-5-carbonyl chloride using method A with 1,4-dioxan as solvent to give the intermediate amide (65%). This is cyclised with methanesulphonic acid in toluene at reflux under standard conditions to give the title compound (46%) as a white crystalline solid m.p. 109-112 C. TLC (SiO2, EtOAc:hexanes 1:1, Rf=0.30). Mass spectrum CI (methane) m/z=326 [M+H]+.

62348-13-4 Isoxazole-5-carbonyl chloride 2736707, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Euro-Celtique, S.A.; US6166041; (2000); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4369-55-5,5-Amino-3-phenylisoxazole,as a common compound, the synthetic route is as follows.

Scheme 42 [0546] A mixture of tert-butyl (lS,2R)-2-(5-bromo-4-cyano-2- fluorophenylamino)cyclohexylcarbamate (165 mg, 0.400 mmol), 5-amino-3-phenylisoxazole (96 mg, 0.600 mmol), sodium phenoxide trihydrate (136 mg, 0.800 mmol), xantphos (30 mg, 0.051 mmol) and Pd2(dba)3 (30 mg, 0.032 mmol) in dioxane (2 mL) was degassed with Ar, then was heated at 170 C for 30 min by microwave. It was concentrated in vacuo. The residue was purified by HPLC to give tert-butyl (lS,2R)-2-(4-cyano-2-fluoro-5-(3- phenylisoxazol-5 -ylamino)phenylamino)cyclohexylcarbamate (40 mg) .

4369-55-5, The synthetic route of 4369-55-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.131052-47-6,(3,5-Dimethylisoxazol-4-yl)methanamine,as a common compound, the synthetic route is as follows.

A mixture of (3,5-dimethylisoxazol-4-yl)methanamine (70 mg, 0.6 mmol), 4- phenoxycarbonylamino-benzoic acid ethyl ester (150 mg, 0.5 mmol) and TEA (0.2 mL, 1.6 mmol) in MeCN (8 mL) was stirred at 80 C for 1 h and then concentrated. The residue was diluted with DCM (40 mL), washed with aq.HC1 (1 N, 20 mL) and Sat.NaHCO3 (20 mL). The DCM solution was dried over Na2SO4, concentrated and purified by Prep-HPLC (NH3.H20) to give ethyl 4-(3-((3,5- dimethylisoxazol-4-yl)methyl)ureido)benzoate (50 mg, yield: 30%) as a white solid. ?H NIVIR (400 IVIHz, DMSO-d6): oe = 8.85 (s, 1H), 7.82 (d, J= 8.8 Hz, 2H), 7.50 (d, J 8.8 Hz, 2H), 6.64 (t, J 5.6 Hz, 1H), 4.26 (q, J= 7.2 Hz, 2H), 4.06 (d, J= 5.6 Hz, 2H), 2.38 (s, 3H), 2.21 (s, 3H), 1.29 (t, J 7.2 Hz, 3H). MS: m/z 318.0 (M+H).

131052-47-6, The synthetic route of 131052-47-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); 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.3405-77-4,5-Methylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of the product from step 2 (57 mg, 0.17 mmol) and 5-methylisoxazole-3-carboxylicacid (23 mg, 0.18 mmol) in CH2C12 (2 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (38 mg, 0.20 mmol) and HOBTH2O (2.5 mg, 0.017 mmol) and the solution stirred at RT for 20 h. 5-Methylisoxazole-3-carboxylic acid (23 mg, 0.18 mmol) and 1-ethyl-3-(3-dimethylamino- propyl)carbodiimide hydrochloride (38 mg, 0.20 mmol) were added and the solution stirred at RT for 3 days. Water (2 mL) was added then the aqueous extracted with CH2C12 (2 mL). The combined organicswere passed through a hydrophobic fit and concentrated in vacuo to leave a colourless residue. Flash chromatography (10-45percent EtOAc-cyclohexane) gave a clear gum (62 mg). Freeze-drying from acetonitrile-water (1:1, 3 mL) left a white solid (56 mg). 1H NMR (400 MHz, DMSO-d6) -3:1 ratio rotamers: 1H NMR (400 MHz, CDC13) 7.42 – 7.35 (2H, m), 7.03 (2H, dd, J=8.0, 8.0 Hz), 6.56 (1H, s), 4.47 (1H, d, J=14.3 Hz), 4.21 – 3.91 (3H, m), 2.97 (1H, d, J=4.0 Hz), 2.36 – 2.34 (6H, m), 1.37 – 1.23 (7H,m), 0.70 (3H, s); MS (ESI): [M+H] 453.2., 3405-77-4

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; CRAWFORD, James J.; BRONNER, Sarah M.; BODIL VAN NIEL, Monique; CRIDLAND, Andrew; GANCIA, Emanuela; HURLEY, Christopher; KILLEN, Jonathan; WARD, Stuart; (108 pag.)WO2016/177760; (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.91252-54-9,Ethyl 5-(tert-butyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

91252-54-9, Step 2: Synthesis of 2-bromo-1-(5-tert-butyl-isoxazol-3-yl)-ethanone The title compound is prepared from 5-tert-butyl-isoxazole-3-carboxylic acid ethyl ester by those skilled in the art by adaptation of a literature procedure (Kaluza et al, Tetrahedron, 2003, 59, 31,5893-5903). To a solution of 5-tert-butyl-isoxazole-3-carboxylic acid ethyl ester (0.5 g, 2.54 mmol) in anhydrous tetrahydrofuran (10 mL) is added under nitrogen dibromomethane (356 muL, 0.88 g, 5.07 mmol). The mixture is cooled to -78 C and 1.6M methyl lithium in diethyl ether (3.2 mL, 5.07 mmol) is added dropwise. The solution is stirred at -78 C for 40 min and then quenched with acetic acid (582 muL, 610 mg, 10.16 mmol). The mixture is warmed to 0 C and poured onto ice/water (40 mL) and extracted with tert-butyl methyl ether (3 x 40 mL). The organic layers are combined, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue is purified by chromatography on silica eluting with a heptane/dichloromethane gradient (1/0 to 1/1) to provide the title compound as a yellow oil (351 mg, 62%), m/z 246 [M+H+]. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.39 (9 H, s), 4.58 (2 H, s), 6.41 (1 H, s).

The synthetic route of 91252-54-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim International GmbH; Boehringer Ingelheim Pharma GmbH & Co. KG; EP2418207; (2012); 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.2510-36-3,3,5-Dimethylisoxasole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

A mixture of 3, 5-dimethyl-isoxazole-4-carboxylic acid (8.1 mg, 0.057 mmol) in dichloromethane (1.5 mL) cooled to [0 oC] was treated with triphenylphosphine (17 mg, 0.063 mmol), and N-chlorosuccinimide (10 mg, 0.074 mmol). This mixture was stirred at [0 oC] for 15 min and at [25 oC] for 20 min. At this time, the reaction was treated with [3-CYCLOPROPYLMETHYL-L- (2-FLUORO-BENZYL)-8- (4-METHYLAMINO-BENZYL)-3,] 7- dihydro-purine-2,6-dione (50 mg, 0.11 mmol). The reaction was then stirred at [25 oC] for 18 h. At this time, the reaction was diluted with dichloromethane (50 mL) and was washed with a saturated aqueous sodium bicarbonate solution [(1 X 10] mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60,230-400 mesh, 2: 98 methanol/ dichloromethane) afforded 3,5-dimethyl-isoxazole-4-carboxylic acid [{4- [3-] [CYCLOPROPYLMETHYL-L-(2-FLUORO-BENZYL)-2,] 6-dioxo-2,3, 6, 7-tetrahydro-lH-purin-8- ylmethyl] -phenyl} -methyl-amide (7.4 mg, 23.2%) as an off-white solid

2510-36-3, The synthetic route of 2510-36-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); 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.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

To a solution of isoxazole-3-carboxylic acid; (119 mg, 1.05 mmol) in DCM (3 mL) was added (COd)2 (190 mg, 1.5 mmol). Then DMF (cat) was added in the mixture. The reaction was stirred at ft for 1 h. A solution of methyl 3-(1-ethyl-4-methyl-1H- benzo [di [1 ,2,3 jtriazol-5-yl)-3-( 1,2,3 ,4-tetrahydroisoquinolin-7-yl)propanoate (80 mg, 0.21 mmol) and TEA (530 mg, 5.25 mmol) in DCM (2 mL) was added to the mixture. The reaction was stirred at ft for another 2 h. The residue was concentrated to give methyl 3-(1- ethyl-4-methyl- 1H-benzo [di [1 ,2,3 jtriazol-5-yl)-3-(2-(isoxazole-3-carbonyl)- 1,2,3,4- tetrahydroisoquinolin-7-yl)propanoate (90 mg, yield: 90%) as white solid. ESI-MS (M+H) :474.2.

3209-71-0, As the paragraph descriping shows that 3209-71-0 is playing an increasingly important role.

Reference£º
Patent; BIOGEN MA INC.; CAPACCI, Andrew, George; DECHANTSREITER, Michael; ENYEDY, Istvan; JONES, John, H.; LIN, Edward, Yin-Shiang; LUCAS, Brian, Stuart; MA, Bin; (273 pag.)WO2018/140876; (2018); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

33282-16-5, 5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid (219 mg, 1.0 mmol) and N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (230 mg, 1.2 mmol) were dissolved in dimethylformamide (5 mL). N,N-Diisopropylethylamine (260 muL, 1.5 mmol) was added and the solution was stirred for 10 minutes. To this solution was added 8-aminoquinaldine (158 mg, 1.0 mmol) and the mixture was stirred for 20 hrs. The mixture was diluted with water and extracted with 2 volumes of ethyl acetate. The organic layers were collected and the solvent was removed by rotary evaporation. The residue was purified by preparative reverse-phase HPLC using a water-acetonitrile gradient to afford compound A24. ESI-MS: m/z 360 [M+H]+.

33282-16-5, 33282-16-5 5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid 1090978, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Dahl, Rusell; (76 pag.)US2019/151303; (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.62348-13-4,Isoxazole-5-carbonyl chloride,as a common compound, the synthetic route is as follows.

62348-13-4, Example 91 N-{[1 ,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1 H-pyrazolo[3,4- b]pyridin-5-yl]methyl}-5-isoxazolecarboxamideA solution of Intermediate 16 (75mg) in anhydrous acetonitrile (1.25ml) was treated with isoxazole-5-carbonyl chloride (33mg) and DIPEA (0.044ml) and stirred at room temperature for 24 hours. The solution was diluted with dichloromethane (10ml), washed with dilute aqueous sodium chloride (2 x 7ml) and evaporated in vacuo to give Example 91 as a yellow sold (104mg). LCMS showed MH+ = 399; TREtau = 1 -98min.

The synthetic route of 62348-13-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/36733; (2007); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem